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'''PRO-LAD''' (or '''6-propyl-6-nor-lysergic acid diethylamide''') is a [[Psychoactive class::psychedelic]] [[hallucinogenic]] drug of the [[Chemical class::lysergamide]] family.
'''N-Propyl''nor''lysergic acid N,N-diethylamide''' (also known as '''6-Propyl-6-''nor''-lysergic acid diethylamide'''<ref name="PCnames>National Center for Biotechnology Information. PubChem Compound Database; CID=44457803, https://pubchem.ncbi.nlm.nih.gov/compound/44457803 (accessed May 5, 2017).</ref>, '''N-Propyl''nor''LSD'''<ref name="PCnames" /> or simply '''PRO-LAD'''<ref name="PCnames" />) is a novel synthetic research [[Psychoactive class::psychedelic]] of the [[Chemical class::lysergamide]] chemical class that is reported to produce a similar, less intense array of [[LSD#Subjective effects|LSD-like]] [[Psychedelic#Subjective effects|psychedelic effects]] when [[Routes of administration|administered]]. It is a close structural homolog of [[LSD]] and was first documented by [[Alexander Shulgin]] in his book [[TiHKAL]] ("Tryptamines I Have Known and Loved"), in which one report remarks that it is "good for humor, even excellent... very good for clear thinking, although not cosmic-type particularly"<ref name="tihkalweb">Shulgin, A., & Shulgin, A. (1991). [https://erowid.org/library/books_online/tihkal/tihkal51.shtml Erowid Online Books: "TIHKAL" - #51. PRO-LAD]. Retrieved April 14, 2017.</ref>


This substance has little to no history of human usage. It was first investigated by Andrew J. Hoffman and David E. Nichols in 1984 as part of a series of LSD analogues, also including [[AL-LAD]] and [[ETH-LAD]]. <ref>https://www.ncbi.nlm.nih.gov/pubmed/4032428 | Hoffman AJ, Nichols DE. Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. J Med Chem. 1985 Sep;28(9):1252-5. PubMed PMID: 4032428</ref>. It was later described as an analog of [[LSD]] by [[Alexander Shulgin]] in the book [[TiHKAL]].<ref>PRO-LAD (TiHKAL / IsomerDesign | https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=51</ref> It is around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.<ref>Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/4032428</ref>
PRO-LAD was first investigated by Andrew J. Hoffman and David E. Nichols in 1984 as part of a series of LSD analogs, which included compounds. [[AL-LAD]] and [[ETH-LAD]]. <ref name="nichols>Hoffman A.J., Nichols D.E. (1985). Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. ''Journal of Medecinal Chemistry'', 28(9), 1252-1255. [https://www.ncbi.nlm.nih.gov/pubmed/4032428 PMID: 4032428]</ref>. It was later described as an analog of [[LSD]] by [[Alexander Shulgin]] in the book [[TiHKAL]]. It has been reported to be around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.<ref name="tihkalweb" />
 
Very little data exists about the pharmacological properties, metabolism, and toxicity of PRO-LAD, and it has little history of human usage. It has recently become appeared on the market alongside [[research chemical]] psychedelic [[lysergamides]] like [[1P-LSD]] and [[AL-LAD]] as a legal, grey-market alternative to [[LSD]], and commercially distributed through online [[research chemical]] vendors, and is considered to be the most difficult to obtain. It is highly advised to approach this unstudied [[hallucinogenic]] substance with the proper amount of precaution and [[Responsible drug use#Hallucinogens|harm reduction practices]] if one chooses to use it.


==Chemistry==
==Chemistry==
PRO-LAD, or 6-propyl-6-nor-lysergic acid diethylamide, is a semi-synthethic alkaloid of the lysergamide famiy. PRO-LAD is a structural analogue of lysergic acid with an N,N-diethylamide functional group bound to R<sub>N</sub> of the chemical structure. This core polycyclic structure is an ergoline derivative and has tryptamine and phenethylamine groups embedded within it. The structure of PRO-LAD contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (nor-lysergic acid).
[[File:Lysergamide1.png|thumb|right|215px|thumb|Substitutive structure of a lysergamide.]]
===Structural composition===
PRO-LAD, or 6-propyl-6-nor-lysergic acid diethylamide, is a semisynthetic alkaloid of the lysergamide chemical class. PRO-LAD is a structural [[analog]] of lysergic acid with an N,N-diethylamide functional group bound to R<sub>N</sub> of the chemical structure. This core polycyclic structure is an indole derivative and has both overlapping tryptamine and phenethylamine skeletons embedded within its molecular structure (although it is principally classified as a tryptamine). The structure of PRO-LAD contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (''nor''-lysergic acid).


===Stereochemistry===
PRO-LAD does not contain a methyl group substituted at R<sub>6</sub> of its nor-lysgeric acid skeleton; this is represented by the nor- prefix. Instead, PRO-LAD is substituted at R<sub>6</sub> with a propyl group. At R<sub>8</sub> of the structure, a N,N-diethyl carboxamide is bound. PRO-LAD is a chiral compound with two stereocenters at R<sub>5</sub> and R<sub>8</sub>. PRO-LAD, also called (+)-D-PRO-LAD, has an absolute configuration of (5R, 8R). PRO-LAD is a derivative of [[LSD]], differing by the addition of two carbons to the methyl group at R<sub>6</sub> of the structure to form a propyl chain. PRO-LAD is also homologous to [[ETH-LAD]], which contains an ethyl substitution at R<sub>6</sub> instead of a propyl chain.
PRO-LAD does not contain a methyl group substituted at R<sub>6</sub> of its nor-lysgeric acid skeleton; this is represented by the nor- prefix. Instead, PRO-LAD is substituted at R<sub>6</sub> with a propyl group. At R<sub>8</sub> of the structure, a N,N-diethyl carboxamide is bound. PRO-LAD is a chiral compound with two stereocenters at R<sub>5</sub> and R<sub>8</sub>. PRO-LAD, also called (+)-D-PRO-LAD, has an absolute configuration of (5R, 8R). PRO-LAD is a derivative of [[LSD]], differing by the addition of two carbons to the methyl group at R<sub>6</sub> of the structure to form a propyl chain. PRO-LAD is also homologous to [[ETH-LAD]], which contains an ethyl substitution at R<sub>6</sub> instead of a propyl chain.
==Pharmacology==
==Pharmacology==
{{Further|Serotonergic psychedelic}}
{{Further|Serotonergic psychedelic}}
PRO-LAD likely acts as a [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] [[Agonist#Agonists|partial agonist]]. The [[psychedelic]] effects are believed to come from PRO-LAD's efficacy at the 5-HT<sub>2A</sub> receptors. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
PRO-LAD likely acts as a [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] [[Agonist#Agonists|partial agonist]]. The [[psychedelic]] effects are believed to come from PRO-LAD's efficacy at the 5-HT<sub>2A</sub> receptors. However, the role of these interactions and how they result in the psychedelic experience continues to remain an object of scientific elucidation.
{{pharmacology}}
==Subjective effects==
==Subjective effects==
{{effectStub}}
{{effectStub}}
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
===Physical effects===
===Physical effects===
*'''[[Effect::Spontaneous tactile sensations]]'''
*'''[[Effect::Spontaneous tactile sensations]]''' - The "body high" of ETH-LAD can be characterized as prominent in comparison to its accompanying visual and cognitive effects. Like LSD, it can behave as a fast-moving, sharp and location specific or generalized tingling sensation, although this feeling is not necessarily pleasant and often manifests in a neutral way. For some, it is manifested spontaneously at different, unpredictable points throughout the trip, but for most, it maintains a steady presence that rises with the onset and hits its limit once the peak has been reached, which many users have reported as feeling "artificial" or "mechanical."
**'''[[Effect::Physical euphoria]]''' - This component can occur with the development of spontaneous tactile sensations, but is not as consistent as it is with [[LSD]], and has more of a tendency to produce strongly dysphoric physical sensations.
*'''[[Effect::Stimulation]]'''
*'''[[Effect::Perception of decreased weight]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Stamina enhancement]]''' - This is generally mild in comparison to traditional [[stimulants]].
*'''[[Effect::Headaches]]'''
*'''[[Effect::Nausea]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Difficulty urinating]]''' or '''[[Effect::Frequent urination]]'''
*'''[[Effect::Temperature regulation suppression]]'''
**'''[[Effect::Increased bodily temperature]]'''
*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Nausea]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Muscle contractions]]'''
*'''[[Effect::Muscle cramps]]''' - This component can occur with the use of any lysergamide or psychedelic, but reports suggest it can be especially pronounced with this substance.
*'''[[Effect::Muscle spasms]]''' - This component can occur with the use of any lysergamide or psychedelic, but reports suggest it can be especially pronounced with this substance.
*'''[[Effect::Olfactory hallucinations]]'''
*'''[[Effect::Sublingual numbing]]'''
*'''[[Effect::Excessive yawning]]'''
*'''[[Effect::Watery eyes]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Vasoconstriction]]'''{{citation needed}}
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Teeth grinding]]''' - This component is considerably less intense when compared with that of substances like [[MDMA]] and happens more readily than with related substances like [[LSD]], perhaps owing to the greater degree of stimulation it produces.
*'''[[Effect::Seizure]]''' - This is a '''very''' rare effect but can likely happen in those predisposed to them, especially while in physically taxing conditions such as being dehydrated, fatigued or undernourished. However, it should be noted that there are no documented cases of seizures occurring with this compound to date.{{citation needed}}


===Cognitive effects===
===Cognitive effects===
The cognitive effects of ETH-LAD can be broken down into several components which progressively intensify proportional to dosage. In comparison to other psychedelics such as [[psilocybin]], [[AL-LAD]] and [[mescaline]], ETH-LAD is often described as significantly more [[stimulating]] and fast-paced in terms of the specific style of thought stream(s) produced and contains a large number of potential effects, which, it should be noted seems to lead to cognitive and general sensory processing overload at moderate to high doses for reasons that are not currently understood.
The most prominent of these cognitive effects generally include:
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Anxiety]]''' & '''[[Effect::Paranoia]]'''
*'''[[Effect::Introspection]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Introspection]]'''
*'''[[Effect::Delusions]]'''
*'''[[Effect::Emotion enhancement]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased sense of humor]]'''
**'''[[Effect::Laughter fits]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought connectivity]]'''
*'''[[Effect::Thought loops]]'''
*'''[[Effect::Language suppression]]'''
*'''[[Effect::Memory suppression]]'''
*'''[[Effect::Memory suppression]]'''
**'''[[Effect::Ego death]]'''
**'''[[Effect::Ego death]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Confusion]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Déjà vu]]'''
*'''[[Effect::Thought loops]]'''
*'''[[Effect::Time distortion]]''' - This component has been reported to be particularly pronounced relative to other psychedelics.
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Unity and interconnectedness]]'''


===Visual effects===
===Visual effects===
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===[[Effect::Geometry]]===
===[[Effect::Geometry]]===
The visual geometry that is commonly present throughout this trip can be generally described as more similar in appearance to that of [[MET]] or [[2C-E]] than [[psilocin]], [[LSA]] or [[DMT]]. It can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as primarily intricate in complexity, algorithmic in form, structured in organization, brightly lit, colourful in scheme, synthetic in feel, multicoloured in scheme, flat in shading, sharp in edges, large in size, fast in speed, smooth in motion, angular in its corners, immersive in-depth and consistent in intensity. At higher dosages, it may almost consistently result in states of [[Effect::8A Geometry|Level 8A]] or [[Level 8B]] visual geometry.{{citation needed}}


====Hallucinatory states====
====Hallucinatory states====
*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::External hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::Internal hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::Internal hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'')


===Auditory effects===
===Auditory effects===
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory enhancement]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory distortion]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
*'''[[Effect::Auditory hallucinations]]'''
 
===Multi-sensory effects===
*'''[[Effect::Synaesthesia]]''' - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.
 
===[[Transpersonal]] effects===
{{Preamble/SpiritualEffects}}
 
*'''[[Spirituality enhancement]]'''
*'''[[Existential self-realization]]'''
*'''[[Feelings of interdependent opposites]]'''
*'''[[Feelings of eternalism]]'''
**'''[[Feelings of self-design]]'''
*'''[[Effect::Unity and interconnectedness]]'''
 
===Combinational effects===
*'''[[Cannabis]]''' - When used in conjunction with cannabis, both the visual and cognitive effects of PRO-LAD can be intensified and extended with extreme efficiency. This should be used with caution if one is not experienced with psychedelics. Many users sometimes report a dramatically more intense visual trip when combining it with [[THC]] concentrates such as hashish as opposed to cannabis flower. However, this can also amplify the [[anxiety]], [[confusion]] and [[psychosis]] producing aspects of both substances significantly, so extreme caution with this combination is advised.
*'''[[Dissociatives]]''' - When used in combination with dissociatives, the geometry, euphoria, dissociation and hallucinatory effects are often greatly enhanced. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] while under the influence of PRO-LAD have significantly more vivid visuals than dissociatives alone present, and more intense [[internal hallucinations]] and [[confusion]].
*'''[[MDMA]]''' - When used in conjunction with MDMA, the physical and cognitive effects of MDMA are amplified. The visual, physical and cognitive effects of LSD are also intensified with an overwhelming euphoric pleasure manifested through uniquely pleasurable body highs and headspaces, and uniquely colorful and awe-inspiring visuals. It is often recommended to wait at least three to four hours after ingesting LSD to take MDMA so as to avoid coming down from the latter while peaking on the former, but positive experiences have been reported with all possible timings. The synergy between these substances is unpredictable (and likely neurotoxic){{citation needed}}, and it is best to start with lower dosages than one would take for both substances individually.
*'''[[Alcohol]]''' - This interaction is not typically recommended due to alcohol’s ability to cause [[dehydration]], [[depression]] and thought disorganization which can negatively affect a trip if taken in high dosages. This combination is however reasonably safe in low doses and when used responsibly, this can often take the edge off a trip as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines, albeit more stressful on the body.
*'''[[Benzodiazepines]]''' - When used in combination with benzodiazepines, benzodiazepines can, depending on the dosage, slightly to completely reduce the intensity of the cognitive, physical and visual effects of a PRO-LAD trip. They are very efficient at stopping [[bad trip]]s at the cost of amnesia and reduced trip intensity. Caution is advised when acquiring them for this purpose due to the very high addiction potential that benzodiazepines possess.
*'''[[Psychedelics]]''' - When used in combination with other psychedelics, each drug's physical, cognitive and visual effects intensify and synergize strongly. The synergy between those substances is unpredictable, and for this reason generally not advised. If choosing to combine psychedelics, it is recommended to start with lower dosages than one would take for either substance individually.


==Toxicity and harm potential==
==Toxicity and harm potential==
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The toxicity and long-term health effects of recreational PRO-LAD do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because PRO-LAD is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried PRO-LAD suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
The toxicity and long-term health effects of recreational PRO-LAD do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because PRO-LAD is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried PRO-LAD suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.


It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.
 
===Tolerance and addiction potential===
===Tolerance and addiction potential===
PRO-LAD is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.  
While no formal studies have been conducted, PRO-LAD is likely [[Addiction potential::not habit-forming]] and it is reasonable to speculate that the desire to use it can actually decrease with repeated administratino. As with most psychedelics, it likely possesses what is considered an intrinsic, self-regulating aspect to it.
 
Tolerance to the effects of PRO-LAD are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::5-7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::14 days]] to be back at baseline (in the absence of further consumption). PRO-LAD presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of PRO-LAD all psychedelics will have a reduced effect.
 
===Dangerous interactions===
Although many substances are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be relatively harmless in low doses of each but can still increase the risk of unpredictable injury or death. [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption. Note that the substances listed below refer to [[LSD]] specifically; however, there is no reason to believe they do not apply equally, if not even more so, to relatively unstudied and structurally similar compounds like AL-LAD as well.
 
*'''[[Tramadol]]''' - Tramadol lowers seizure threshold<ref>Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089</ref> and psychedelics may cause occasional seizures.<ref name"tripsit">Tripsit Factsheets - LSD | http://drugs.tripsit.me/lsd</ref><ref>Fisher, D. D., & Ungerleider, J. T. (1967). [https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1502729/ Grand mal seizures following ingestion of LSD]. California Medicine, 106(3), 210. PMCID: PMC1502729</ref><ref>Question ID: 2837 (Ask Erowid) | https://www.erowid.org/ask/ask.php?ID=2837</ref>
*'''[[Stimulants]]''' - Stimulants may provoke anxiety or [[thought loops]].<ref>Tripsit Factsheets - LSD | http://drugs.tripsit.me/lsd</ref>
*'''[https://en.wikipedia.org/wiki/Lithium_(medication) Lithium]''' - Individuals who take lithium for bipolar disorder or other psychiatric conditions should not take LSD. There are numerous anecdotal reports of seizures and or unsafe psychosis from this combination.<ref>https://erowid.org/chemicals/lsd/lsd_interactions.shtml | LSD Interactions by Erowid</ref><ref>Wanderli. [https://erowid.org/experiences/exp.php?ID=83935 "A Nice Little Trip to the Hospital: An Experience with Lithium & LSD (ID 83935)"]. Erowid.org. Oct 3, 2010.</ref><ref>MissDja1a. [https://erowid.org/experiences/exp.php?ID=75153 "Having a Seizure and Passing Out: An Experience with Lithium & LSD (ID 75153)"]. Erowid.org. Dec 16, 2008. </ref><ref>Reddit account of seizure on LSD + Lithium | https://www.reddit.com/r/Psychonaut/comments/17uspp/please_read_a_cautionary_tale_concerning_lsd/</ref>


Tolerance to the effects of PRO-LAD are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). PRO-LAD presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of PRO-LAD all psychedelics will have a reduced effect.
==Legal issues==
==Legal issues==
{{LegalStub}}
{{LegalStub}}
Line 83: Line 160:


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use (Hallucinogens)]]
*[[Research chemical]]
*[[Hallucinogens]]
*[[Psychedelic]]
*[[Lysergamide]]
*[[Lysergamide]]
*[[Psychedelic]]
*[[LSD]]
*[[AL-LAD]]
*[[AL-LAD]]
*[[ETH-LAD]]
*[[ETH-LAD]]
*[[1P-LSD]]
*[[LSD]]


==External links==
==External links==
*[https://en.wikipedia.org/wiki/PRO-LAD PRO-LAD (Wikipedia)]
*[https://en.wikipedia.org/wiki/PRO-LAD PRO-LAD (Wikipedia)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=51 PRO-LAD (TiHKAL)]
*[https://erowid.org/library/books_online/tihkal/tihkal.shtml Erowid Online Books: "TIHKAL" - #51 PRO-LAD]


==Literature==
==Literature==
* Nichols, D. E. (2016). '''''Psychedelics''''', (April), 264–355.https://doi.org/10.1124/pr.115.011478
* Hoffman, A. J., & Nichols, D. E. (1985). '''''Synthesis and LSD-like discriminative stimulus properties in a series of N (6)-alkyl norlysergic acid N, N-diethylamide derivatives.''''' ''Journal of Medicinal Chemistry'', 28(9), 1252-1255. https://doi.org/10.1021/jm00147a022.
* Andrew J. Hoffman, David E. Nichols. ''''Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives.''''' In: ''Journal of Medicinal Chemistry.'' 28, 1985, p.&nbsp;1252–1255, doi:10.1021/jm00147a022.
* Watts, V. J., Mailman, R. B., Lawler, C. P., Neve, K. A., & Nichols, D. E. (1995). '''''LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors'''''. ''Psychopharmacology'', 118(4), 401-409. https://doi.org/10.1007/BF02245940.
* V. J. Watts, R. B. Mailman, C. P. Lawler, K. A. Neve, D. E. Nichols: ''LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors.'' In: ''Psychopharmacology.'' 118, 1995, p.&nbsp;401–409, doi:10.1007/BF02245940.
* Niwaguchi, T., Nakahara, Y., & Ishii, H. (1976). '''''Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds.''''' ''Yakugaku Zasshi: Journal of the Pharmaceutical Society of Japan'', 96(5), 673-678. PMID 987200.
* T. Niwaguchi, Y. Nakahara, H. Ishii: '''''Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds.''''' In: ''Yakugaku Zasshi.'' Vol. 96, No. 5, May 1976, p.&nbsp;673–678,  PMID 987200.
* Pfaff, R. C., Huang, X., Marona-Lewicka, D., Oberlender, R., & Nichols, D. E. (1994). '''''[http://archives.drugabuse.gov/pdf/monographs/146.pdf Lysergamides Revisited.]''''' ''NIDA Research Monograph'', 146, 52-73. PMID: 8742794.
* Robert C. Pfaff, Xuemei Huang, Danuta Marona-Lewicka, Robert Oberlender and David E. Nichols: ''[http://archives.drugabuse.gov/pdf/monographs/146.pdf Lysergamides Revisited.]'' In: ''NIDA Research Monograph 146: Hallucinogens: An Update.'' p.&nbsp;52, 1994, United States Department of Health and Human Services.
* Vollenweider, F. X., & Kometer, M. (2010). '''''The neurobiology of psychedelic drugs: implications for the treatment of mood disorders.''''' Nature Publishing Group, 11(9), 642–651. https://doi.org/10.1038/nrn2884
* Nichols, D. E. (2004). '''''Hallucinogens'''''. Pharmacology and Therapeutics, 101(2), 131–181. https://doi.org/10.1016/j.pharmthera.2003.11.002
* Halberstadt, A. L. (2015). '''''Recent advances in the neuropsychopharmacology of serotonergic hallucinogens.''''' Behavioral Brain Research, 277, 99–120. https://doi.org/10.1016/j.bbr.2014.07.016


==References==
==References==
<references/>
<references/>
[[Category:Substance]]
 
[[Category:Psychoactive substance]]
[[Category:Research chemical]]
[[Category:Hallucinogen]]
[[Category:Psychedelic]]
[[Category:Psychedelic]]
[[Category:Lysergamide]]
[[Category:Lysergamide]]
[[Category:Psychoactive substance]]
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PRO-LAD
Chemical Nomenclature
Common names PRO-LAD
Substitutive name 6-Propyl-6-nor-lysergic acid diethylamide
Systematic name (8β)-N,N-Diethyl-6-propyl-9,10-didehydroergoline-8-carboxamide
Class Membership
Psychoactive class Psychedelic
Chemical class Lysergamide
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



⇣ Oral
Dosage
Threshold 20 µg
Light 50 - 100 µg
Common 100 - 200 µg
Strong 200 - 350 µg
Heavy 350 µg +
Duration
Total 6 - 8 hours
Onset 30 - 45 minutes









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
Summary sheet: PRO-LAD

N-Propylnorlysergic acid N,N-diethylamide (also known as 6-Propyl-6-nor-lysergic acid diethylamide[1], N-PropylnorLSD[1] or simply PRO-LAD[1]) is a novel synthetic research psychedelic of the lysergamide chemical class that is reported to produce a similar, less intense array of LSD-like psychedelic effects when administered. It is a close structural homolog of LSD and was first documented by Alexander Shulgin in his book TiHKAL ("Tryptamines I Have Known and Loved"), in which one report remarks that it is "good for humor, even excellent... very good for clear thinking, although not cosmic-type particularly"[2]

PRO-LAD was first investigated by Andrew J. Hoffman and David E. Nichols in 1984 as part of a series of LSD analogs, which included compounds. AL-LAD and ETH-LAD. [3]. It was later described as an analog of LSD by Alexander Shulgin in the book TiHKAL. It has been reported to be around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.[2]

Very little data exists about the pharmacological properties, metabolism, and toxicity of PRO-LAD, and it has little history of human usage. It has recently become appeared on the market alongside research chemical psychedelic lysergamides like 1P-LSD and AL-LAD as a legal, grey-market alternative to LSD, and commercially distributed through online research chemical vendors, and is considered to be the most difficult to obtain. It is highly advised to approach this unstudied hallucinogenic substance with the proper amount of precaution and harm reduction practices if one chooses to use it.

Chemistry

Substitutive structure of a lysergamide.

Structural composition

PRO-LAD, or 6-propyl-6-nor-lysergic acid diethylamide, is a semisynthetic alkaloid of the lysergamide chemical class. PRO-LAD is a structural analog of lysergic acid with an N,N-diethylamide functional group bound to RN of the chemical structure. This core polycyclic structure is an indole derivative and has both overlapping tryptamine and phenethylamine skeletons embedded within its molecular structure (although it is principally classified as a tryptamine). The structure of PRO-LAD contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (nor-lysergic acid).

Stereochemistry

PRO-LAD does not contain a methyl group substituted at R6 of its nor-lysgeric acid skeleton; this is represented by the nor- prefix. Instead, PRO-LAD is substituted at R6 with a propyl group. At R8 of the structure, a N,N-diethyl carboxamide is bound. PRO-LAD is a chiral compound with two stereocenters at R5 and R8. PRO-LAD, also called (+)-D-PRO-LAD, has an absolute configuration of (5R, 8R). PRO-LAD is a derivative of LSD, differing by the addition of two carbons to the methyl group at R6 of the structure to form a propyl chain. PRO-LAD is also homologous to ETH-LAD, which contains an ethyl substitution at R6 instead of a propyl chain.

Pharmacology

Further information: Serotonergic psychedelic

PRO-LAD likely acts as a 5-HT2A partial agonist. The psychedelic effects are believed to come from PRO-LAD's efficacy at the 5-HT2A receptors. However, the role of these interactions and how they result in the psychedelic experience continues to remain an object of scientific elucidation.

This pharmacology section is incomplete.

You can help by adding to it.

Subjective effects

 This subjective effects section is a stub.

As such, it is still in progress and may contain incomplete or wrong information.

You can help by expanding or correcting it.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects

Cognitive effects

The cognitive effects of ETH-LAD can be broken down into several components which progressively intensify proportional to dosage. In comparison to other psychedelics such as psilocybin, AL-LAD and mescaline, ETH-LAD is often described as significantly more stimulating and fast-paced in terms of the specific style of thought stream(s) produced and contains a large number of potential effects, which, it should be noted seems to lead to cognitive and general sensory processing overload at moderate to high doses for reasons that are not currently understood.

The most prominent of these cognitive effects generally include:

Visual effects

Enhancements

Distortions

Geometry

The visual geometry that is commonly present throughout this trip can be generally described as more similar in appearance to that of MET or 2C-E than psilocin, LSA or DMT. It can be comprehensively described through its variations as primarily intricate in complexity, algorithmic in form, structured in organization, brightly lit, colourful in scheme, synthetic in feel, multicoloured in scheme, flat in shading, sharp in edges, large in size, fast in speed, smooth in motion, angular in its corners, immersive in-depth and consistent in intensity. At higher dosages, it may almost consistently result in states of Level 8A or Level 8B visual geometry.[citation needed]

Hallucinatory states

Auditory effects

Multi-sensory effects

  • Synaesthesia - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.

Transpersonal effects

It should be noted that these effects are the rarest and least reproducible those that can occur during a psychedelic experience. They are considered unique in that that simply taking more of the substance does not necessarily increase the chance they will occur, and are said to rely more on contextual factors such as the user's set and setting rather than the substance or dose itself. Their fullest manifestations are sometimes called "peak", "transcendent" or "transformative" experiences; however, they can still occur on a conceptual or cognitive level that can leave a lasting positive impact on the user.

Combinational effects

  • Cannabis - When used in conjunction with cannabis, both the visual and cognitive effects of PRO-LAD can be intensified and extended with extreme efficiency. This should be used with caution if one is not experienced with psychedelics. Many users sometimes report a dramatically more intense visual trip when combining it with THC concentrates such as hashish as opposed to cannabis flower. However, this can also amplify the anxiety, confusion and psychosis producing aspects of both substances significantly, so extreme caution with this combination is advised.
  • Dissociatives - When used in combination with dissociatives, the geometry, euphoria, dissociation and hallucinatory effects are often greatly enhanced. Dissociative-induced holes, spaces, and voids while under the influence of PRO-LAD have significantly more vivid visuals than dissociatives alone present, and more intense internal hallucinations and confusion.
  • MDMA - When used in conjunction with MDMA, the physical and cognitive effects of MDMA are amplified. The visual, physical and cognitive effects of LSD are also intensified with an overwhelming euphoric pleasure manifested through uniquely pleasurable body highs and headspaces, and uniquely colorful and awe-inspiring visuals. It is often recommended to wait at least three to four hours after ingesting LSD to take MDMA so as to avoid coming down from the latter while peaking on the former, but positive experiences have been reported with all possible timings. The synergy between these substances is unpredictable (and likely neurotoxic)[citation needed], and it is best to start with lower dosages than one would take for both substances individually.
  • Alcohol - This interaction is not typically recommended due to alcohol’s ability to cause dehydration, depression and thought disorganization which can negatively affect a trip if taken in high dosages. This combination is however reasonably safe in low doses and when used responsibly, this can often take the edge off a trip as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines, albeit more stressful on the body.
  • Benzodiazepines - When used in combination with benzodiazepines, benzodiazepines can, depending on the dosage, slightly to completely reduce the intensity of the cognitive, physical and visual effects of a PRO-LAD trip. They are very efficient at stopping bad trips at the cost of amnesia and reduced trip intensity. Caution is advised when acquiring them for this purpose due to the very high addiction potential that benzodiazepines possess.
  • Psychedelics - When used in combination with other psychedelics, each drug's physical, cognitive and visual effects intensify and synergize strongly. The synergy between those substances is unpredictable, and for this reason generally not advised. If choosing to combine psychedelics, it is recommended to start with lower dosages than one would take for either substance individually.

Toxicity and harm potential

Further information: Research chemicals § Toxicity and harm potential, and Responsible use § Hallucinogens

The toxicity and long-term health effects of recreational PRO-LAD do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because PRO-LAD is a research chemical with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried PRO-LAD suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

It is strongly recommended that one use harm reduction practices when using this substance.

Tolerance and addiction potential

While no formal studies have been conducted, PRO-LAD is likely not habit-forming and it is reasonable to speculate that the desire to use it can actually decrease with repeated administratino. As with most psychedelics, it likely possesses what is considered an intrinsic, self-regulating aspect to it.

Tolerance to the effects of PRO-LAD are built almost immediately after ingestion. After that, it takes about 5-7 days for the tolerance to be reduced to half and 14 days to be back at baseline (in the absence of further consumption). PRO-LAD presents cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of PRO-LAD all psychedelics will have a reduced effect.

Dangerous interactions

Although many substances are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be relatively harmless in low doses of each but can still increase the risk of unpredictable injury or death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption. Note that the substances listed below refer to LSD specifically; however, there is no reason to believe they do not apply equally, if not even more so, to relatively unstudied and structurally similar compounds like AL-LAD as well.

  • Tramadol - Tramadol lowers seizure threshold[4] and psychedelics may cause occasional seizures.[5][6][7]
  • Stimulants - Stimulants may provoke anxiety or thought loops.[8]
  • Lithium - Individuals who take lithium for bipolar disorder or other psychiatric conditions should not take LSD. There are numerous anecdotal reports of seizures and or unsafe psychosis from this combination.[9][10][11][12]

This legality section is a stub.

As such, it may contain incomplete or wrong information. You can help by expanding it.

  • United Kingdom: As of January 7th, 2015, PRO-LAD is specifically named in the U.K. Misuse of Drugs Act as a Class A drug.[13]
  • Switzerland: On December 1, 2015, Switzerland added PRO-LAD to the list of controlled substances.[14]
  • Latvia - PRO-LAD is illegal in Latvia. Although it isn't officially scheduled, it is controlled as an LSD structural analog due to an amendment made on June 1th, 2015.[15]

See also

Literature

  • Hoffman, A. J., & Nichols, D. E. (1985). Synthesis and LSD-like discriminative stimulus properties in a series of N (6)-alkyl norlysergic acid N, N-diethylamide derivatives. Journal of Medicinal Chemistry, 28(9), 1252-1255. https://doi.org/10.1021/jm00147a022.
  • Watts, V. J., Mailman, R. B., Lawler, C. P., Neve, K. A., & Nichols, D. E. (1995). LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors. Psychopharmacology, 118(4), 401-409. https://doi.org/10.1007/BF02245940.
  • Niwaguchi, T., Nakahara, Y., & Ishii, H. (1976). Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds. Yakugaku Zasshi: Journal of the Pharmaceutical Society of Japan, 96(5), 673-678. PMID 987200.
  • Pfaff, R. C., Huang, X., Marona-Lewicka, D., Oberlender, R., & Nichols, D. E. (1994). Lysergamides Revisited. NIDA Research Monograph, 146, 52-73. PMID: 8742794.

References

  1. ↑ 1.0 1.1 1.2 National Center for Biotechnology Information. PubChem Compound Database; CID=44457803, https://pubchem.ncbi.nlm.nih.gov/compound/44457803 (accessed May 5, 2017).
  2. ↑ 2.0 2.1 Shulgin, A., & Shulgin, A. (1991). Erowid Online Books: "TIHKAL" - #51. PRO-LAD. Retrieved April 14, 2017.
  3. ↑ Hoffman A.J., Nichols D.E. (1985). Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. Journal of Medecinal Chemistry, 28(9), 1252-1255. PMID: 4032428
  4. ↑ Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089
  5. ↑ Tripsit Factsheets - LSD | http://drugs.tripsit.me/lsd
  6. ↑ Fisher, D. D., & Ungerleider, J. T. (1967). Grand mal seizures following ingestion of LSD. California Medicine, 106(3), 210. PMCID: PMC1502729
  7. ↑ Question ID: 2837 (Ask Erowid) | https://www.erowid.org/ask/ask.php?ID=2837
  8. ↑ Tripsit Factsheets - LSD | http://drugs.tripsit.me/lsd
  9. ↑ https://erowid.org/chemicals/lsd/lsd_interactions.shtml | LSD Interactions by Erowid
  10. ↑ Wanderli. "A Nice Little Trip to the Hospital: An Experience with Lithium & LSD (ID 83935)". Erowid.org. Oct 3, 2010.
  11. ↑ MissDja1a. "Having a Seizure and Passing Out: An Experience with Lithium & LSD (ID 75153)". Erowid.org. Dec 16, 2008.
  12. ↑ Reddit account of seizure on LSD + Lithium | https://www.reddit.com/r/Psychonaut/comments/17uspp/please_read_a_cautionary_tale_concerning_lsd/
  13. ↑ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014. 
  14. ↑ https://www.admin.ch/opc/de/official-compilation/2015/5093.pdf
  15. ↑ Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2.4.punkts) | http://likumi.lv/doc.php?id=121086


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