AL-LAD: Difference between revisions
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'''6-Allyl-6-nor-lysergic acid diethylamide''' (also known as '''N-allyl-''nor''-lysergic acid N,N-diethylamide''', '''N-allyl''-nor''-LSD''', or commonly as '''AL-LAD''') is a novel [[Psychoactive class::psychedelic]] substance of the [[chemical class::lysergamide]] class. AL-LAD is chemically similar to [[LSD]] and has a similar mechanism of action, working primarily by binding to [[serotonin]] receptors in the brain. | '''6-Allyl-6-nor-lysergic acid diethylamide''' (also known as '''N-allyl-''nor''-lysergic acid N,N-diethylamide''', '''N-allyl''-nor''-LSD''', or commonly as '''AL-LAD''') is a novel [[Psychoactive class::psychedelic]] substance of the [[chemical class::lysergamide]] class. AL-LAD is chemically similar to [[LSD]] and has a similar mechanism of action, working primarily by binding to [[serotonin]] receptors in the brain. | ||
AL-LAD was first investigated in 1984 by Andrew J. Hoffman and [[David Nichols]] as part of a series of LSD analogs, which also included [[ETH-LAD]] and [[PRO-LAD]].<ref name="nichols">{{cite journal|last1=Hoffman|first1=Andrew J.|last2=Nichols|first2=David E.|author-link2=David E. Nichols|title=Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives|journal=Journal of Medicinal Chemistry|volume=28|issue=9|pages=1252-1255|year=1985|doi=10.1021/jm00147a022|issn=0022-2623}}</ref> Its activity in humans was later documented by [[Alexander Shulgin]] in his book [[TiHKAL]] ("Tryptamines I Have Known and Loved"), in which it is described as "considerably less dramatic".<ref name="TiKHAL">{{cite book|title= | AL-LAD was first investigated in 1984 by Andrew J. Hoffman and [[David Nichols]] as part of a series of LSD analogs, which also included [[ETH-LAD]] and [[PRO-LAD]].<ref name="nichols">{{cite journal|last1=Hoffman|first1=Andrew J.|last2=Nichols|first2=David E.|author-link2=David E. Nichols|title=Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives|journal=Journal of Medicinal Chemistry|volume=28|issue=9|pages=1252-1255|year=1985|doi=10.1021/jm00147a022|issn=0022-2623}}</ref> Its activity in humans was later documented by [[Alexander Shulgin]] in his book [[TiHKAL]] ("Tryptamines I Have Known and Loved"), in which it is described as "considerably less dramatic".<ref name="TiKHAL">{{cite book|title=TiHKAL: The Continuation|title-link=TiHKAL|last1=Shulgin|first1=Alexander|last2=Shulgin|first2=Ann|author-link1=Alexander Shulgin|year=1997|publisher=Transform Press|location=United States|isbn=0-9630096-9-9|oclc=38503252|chapter-url=https://erowid.org/library/books_online/tihkal/tihkal01.shtml|chapter=#1. AL-LAD}}</ref> In 2013, AL-LAD appeared for sale on the [[research chemical]] market,<ref name="Brandt2015">{{cite journal|last1=Brandt|first1=S. D.|last2=Kavanagh|first2=P. V.|last3=Westphal|first3=F.|last4=Elliott|first4=S. P.|last5=Wallach|first5=J.|last6=Colestock|first6=T.|last7=Burrow|first7=T. E.|last8=Chapman|first8=S. J.|last9=Stratford|first9=A.|last10=Nichols|first10=D. E.|author-link10=David E. Nichols|last11=Halberstadt|first11=A. L.|year=2016|title=Return of the lysergamides. Part II: Analytical and behavioural characterization of N<sup>6</sup>‐allyl‐6‐norlysergic acid diethylamide (AL‐LAD) and (2´''S'',4´''S'')‐lysergic acid 2,4‐dimethylazetidide (LSZ)|journal=Drug Testing and Analysis|volume=9|issue=1|pages=38-50|doi=10.1002/dta.1985|issn=1942-7603}}</ref> where it has been commonly marketed alongside lysergamides such as [[1P-LSD]], [[ALD-52]] and [[ETH-LAD]] as a legal, grey-market alternative to LSD. | ||
User reports describe the effects of AL-LAD as similar to those of LSD with some subtle differences. It is thought to either be equally or moderately less potent than [[LSD]] itself, with an active dose reported at between 75 and 150 micrograms. It is often described as being more visually-oriented but with a less introspective headspace. It also has a moderately shorter duration and is generally considered to be a less [[anxiety]]-provoking and challenging version of LSD. | User reports describe the effects of AL-LAD as similar to those of LSD with some subtle differences. It is thought to either be equally or moderately less potent than [[LSD]] itself, with an active dose reported at between 75 and 150 micrograms. It is often described as being more visually-oriented but with a less introspective headspace. It also has a moderately shorter duration and is generally considered to be a less [[anxiety]]-provoking and challenging version of LSD. | ||
Revision as of 00:16, 2 January 2020
| Summary sheet: AL-LAD |
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||||
| Common names | AL-LAD, Aladdin | ||||||||||||||||||||||||||||||||
| Substitutive name | 6-Allyl-6-nor-lysergic acid diethylamide | ||||||||||||||||||||||||||||||||
| Systematic name | (6aR,9R)-N,N-Diethyl-7-(prop-2-en-1-yl)-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide | ||||||||||||||||||||||||||||||||
| Class Membership | |||||||||||||||||||||||||||||||||
| Psychoactive class | Psychedelic | ||||||||||||||||||||||||||||||||
| Chemical class | Lysergamide | ||||||||||||||||||||||||||||||||
| Routes of Administration | |||||||||||||||||||||||||||||||||
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6-Allyl-6-nor-lysergic acid diethylamide (also known as N-allyl-nor-lysergic acid N,N-diethylamide, N-allyl-nor-LSD, or commonly as AL-LAD) is a novel psychedelic substance of the lysergamide class. AL-LAD is chemically similar to LSD and has a similar mechanism of action, working primarily by binding to serotonin receptors in the brain.
AL-LAD was first investigated in 1984 by Andrew J. Hoffman and David Nichols as part of a series of LSD analogs, which also included ETH-LAD and PRO-LAD.[1] Its activity in humans was later documented by Alexander Shulgin in his book TiHKAL ("Tryptamines I Have Known and Loved"), in which it is described as "considerably less dramatic".[2] In 2013, AL-LAD appeared for sale on the research chemical market,[3] where it has been commonly marketed alongside lysergamides such as 1P-LSD, ALD-52 and ETH-LAD as a legal, grey-market alternative to LSD.
User reports describe the effects of AL-LAD as similar to those of LSD with some subtle differences. It is thought to either be equally or moderately less potent than LSD itself, with an active dose reported at between 75 and 150 micrograms. It is often described as being more visually-oriented but with a less introspective headspace. It also has a moderately shorter duration and is generally considered to be a less anxiety-provoking and challenging version of LSD.
Very little data exists about the pharmacological properties, metabolism, and toxicity of AL-LAD. While it is often characterized by users as being generally more recreational and non-threatening compared to LSD, it is highly advised to approach this highly potent hallucinogenic substance with the proper amount of precaution and harm reduction practices if using it.
Chemistry
AL-LAD, or 6-allyl-6-nor-lysergic acid diethylamide, is a semisynthetic alkaloid of the lysergamide family. AL-LAD is a structural analog of lysergic acid, with an N,N-diethylamide functional group bound to RN of the chemical structure. AL-LAD's chemical structure contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (nor-lysergic acid). Unlike LSD, AL-LAD does not contain a methyl group substituted at R6 of its nor-lysergic acid skeleton, this is represented by the nor- prefix. Instead, AL-LAD is substituted at R6 with an allyl group comprised of a methylene bridge bound to a vinyl substituent. At carbon 8 of the quinoline a N,N-diethyl carboxamide is bound.
AL-LAD is a chiral compound with two stereocenters at R5 and R8. AL-LAD, also called (+)-D-AL-LAD, has an absolute configuration of (5R, 8R). The three other stereoisomers of AL-LAD do not have psychoactive properties.Cite error: Closing </ref> missing for <ref> tag[4][5] and this may extend to AL-LAD.
Experience reports
There are currently 3 anecdotal reports which describe the effects of this compound within our experience index.
- Experience:150mcg AL-LAD: First trip, intense Visuals and Good Vibes
- Experience:300µg AL-LAD - Don't worry, because you're everyone!
- Experience:AL-LAD - Microdose out of depression
Additional experience reports can be found here:
Toxicity and harm potential
The toxicity and long-term health effects of recreational AL-LAD use do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because AL-LAD is a research chemical with very little history of human usage.
The body of anecdotal reports suggests that there are no negative health effects attributed to simply trying the substance 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.
As with other psychedelic substances, there are relatively few physical side effects that have been reported associated with acute AL-LAD exposure. Although no formal studies have been conducted, it is likely that as with LSD itself, AL-LAD is able to be considered non-addictive, with an extremely low toxicity relative to dose.[6] It is also likely that as with LSD, there are little to no negative physical, cognitive, psychiatric or other toxic consequences associated with acute AL-LAD exposure.
However, as with LSD and psychedelics in general, it is possible that AL-LAD can act as a potential trigger for those with underlying psychiatric conditions. Those with a personal or family history of mental illness are generally advised not to use this substance, particularly outside of a supervised medical setting.
It is strongly recommended that one uses harm reduction practices when using this substance.
Tolerance and addiction potential
Although no formal studies have been conducted, it is not unreasonable to assume that as with LSD itself, AL-LAD is not habit-forming and that the desire to use it can actually decrease with use.
Tolerance to the effects of AL-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). AL-LAD presents cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the use of AL-LAD all psychedelics will have a reduced effect.
Overdose
The LD50 of AL-LAD is unknown. Adverse psychological reactions are common especially at higher dosages. Some of these include anxiety, delusions, panic attacks and more rarely seizures. Medical attention is usually only needed if suspected of severe psychotic episodes or “fake acid” (such as 25i-NBOMe or DOB). Administration of benzodiazepines or antipsychotics can help to relieve the negative cognitive effects of AL-LAD.
Dangerous interactions
Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
- [[Wikipedia:Lithium_(medication)|DangerousInteraction::Lithium]] - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
- "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of AL-LAD. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
- "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Stimulants like amphetamine, cocaine or methylphenidate affect many parts of the brain and alter dopaminergic function. This combination can increase the risk of anxiety, paranoia, panic attacks, and thought loops. This interaction may also result in an elevated risk of mania and psychosis.[citation needed]
- "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is well-documented to lower the seizure threshold[7] and psychedelics may act to trigger seizures in susceptible individuals.[citation needed]
Legal status
AL-LAD is currently a gray area compound within many parts of the world. This means that it is not known to be specifically illegal within most countries, but people may still be charged for its possession under certain circumstances such as under analog laws and with the intent to sell or consume.
- Austria: AL-LAD is technically not illegal but it may fall in the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich) as an analogue of LSD. [citation needed]
- Denmark: As of August 25, 2015, AL-LAD is specifically named on the list of illegal substances.[8]
- Germany: AL-LAD is controlled under the NpSG (New Psychoactive Substances Act)[9] as of July 18, 2019.[10] Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.[11]
- Latvia: AL-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 1, 2015.[12]
- Sweden: Following its sale as a designer drug, AL-LAD was made illegal in Sweden on January 26, 2016.[13]
- Switzerland: 21 substances, including AL-LAD, were added to the list of illegal substances including on December 1, 2015.[14]
- United Kingdom: As of January 7, 2015, AL-LAD is specifically named in the U.K. Misuse of Drugs Act as a Class A controlled substance.[15]
- United States: AL-LAD is unscheduled but can be considered to be an analogue of LSD, which would make it illegal to possess for human consumption under the Federal Analogue Act.[citation needed]
See also
External links
Discussion
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
- ↑ Hoffman, Andrew J.; Nichols, David 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. doi:10.1021/jm00147a022. ISSN 0022-2623.
- ↑ Shulgin, Alexander; Shulgin, Ann (1997). "#1. AL-LAD". TiHKAL: The Continuation. United States: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
- ↑ Brandt, S. D.; Kavanagh, P. V.; Westphal, F.; Elliott, S. P.; Wallach, J.; Colestock, T.; Burrow, T. E.; Chapman, S. J.; Stratford, A.; Nichols, D. E.; Halberstadt, A. L. (2016). "Return of the lysergamides. Part II: Analytical and behavioural characterization of N6‐allyl‐6‐norlysergic acid diethylamide (AL‐LAD) and (2´S,4´S)‐lysergic acid 2,4‐dimethylazetidide (LSZ)". Drug Testing and Analysis. 9 (1): 38–50. doi:10.1002/dta.1985. ISSN 1942-7603.
- ↑ Gudelsky, Gary A.; Yamamoto, Bryan; Nash, J. Frank (1994). "Potentiation of 3,4-methylenedioxymethamphetamine-induced dopamine release and serotonin neurotoxicity by 5-HT2 receptor agonists". European Journal of Pharmacology. 264 (3): 325–330. doi:10.1016/0014-2999(94)90669-6. ISSN 0014-2999.
- ↑ Capela, J. P.; Fernandes, E.; Remião, F.; Bastos, M. L.; Meisel, A.; Carvalho, F. (2007). "Ecstasy induces apoptosis via 5-HT2A-receptor stimulation in cortical neurons". Neurotoxicology. 28 (4): 868–875. doi:10.1016/j.neuro.2007.04.005. ISSN 0161-813X. PMID 17572501.
- ↑ Passie, T.; Halpern, J. H.; Stichtenoth, D. O.; Emrich, H. M.; Hintzen, A. "The Pharmacology of Lysergic Acid Diethylamide: A Review" (PDF). CNS Neuroscience & Therapeutics. 14: 295–314. doi:10.1111/j.1755-5949.2008.00059.x. ISSN 1755-5930. Archived from the original (PDF) on May 1, 2013. Retrieved January 1, 2020.
- ↑ 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. ISSN 1556-9039.
- ↑ "Bekendtgørelse om euforiserende stoffer - ni nye stoffer tilføjet" (in dansk). Danish Medicines Ageny. August 31, 2015. Retrieved January 1, 2020.
- ↑ "Anlage NpSG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
- ↑ "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27 (in Deutsch). Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. Retrieved January 1, 2020.
- ↑ "§ 4 NpSG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 10, 2019.
- ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in latviešu). Latvijas Vēstnesis. November 10, 2005. Retrieved January 1, 2020.
- ↑ "31 nya substanser klassas som narkotika eller hälsofarlig vara" (in svenska). Folkhälsomyndigheten. January 26, 2016. Retrieved January 1, 2020.
- ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel,psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien: Änderung vom 2. November 2015" (PDF) (in Deutsch). Federal Chancellery of Switzerland. Retrieved January 1, 2020.
- ↑ Advisory Council on the Misuse of Drugs (June 10, 2014). "Update of the generic definition for tryptamines" (PDF). Government Digital Service. p. 12. Retrieved January 1, 2020.