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m added a "likely" to the unsubstantiated claim that Cyclazodone is a TAAR1 agonist
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{{SummarySheet}}
{{SummarySheet}}
{{SubstanceBox/Cyclazodone}}
{{SubstanceBox/Cyclazodone}}
'''N-Cyclopropylpemoline''' (also known as '''Cyclazodone''') is a novel [[psychoactive class::stimulant]] substance of the [[chemical class::4-oxazolidinone]] class. It is structurally related to [[pemoline]] and [[4-methylaminorex]]. The mechanism of action involves promoting the release of [[dopamine]] and [[norepinephrine]] in the brain.
'''N-Cyclopropylpemoline''' (also known as '''Cyclazodone''') is a novel [[psychoactive class::stimulant]] substance of the [[chemical class::4-oxazolidinone]] class that produces [[stimulating]] and [[focus enhancement|focus enhancing]] effects when [[administered]]. It is structurally related to [[pemoline]] and [[4-methylaminorex]].
Cyclazodone was developed in the 1960s by the American Cyanamid Company. Its non-clinical use has only found recent attention as a [[research chemical]] study aid. It should be noted that the lack of pharmacological data and extremely limited history of human usage pose considerable concern regarding its long-term use as a substitute for prescription stimulants.
Cyclazodone was developed in the 1960s by the American Cyanamid Company. Its non-clinical use has only found recent attention as a [[research chemical]] study aid. It should be noted that the lack of pharmacological data and extremely limited history of human usage pose considerable concern regarding its long-term use as a substitute for prescription stimulants.
[[Subjective effects]] include [[stimulation]], [[focus enhancement]], [[stamina enhancement]], [[increased blood pressure]], and mild [[euphoria]]. Some anecdotal reports suggest that [[cyclazodone]] and its parent compound [[pemoline]] may have nootropic properties similar to central nervous system stimulants such as [[methylphenidate]] and [[amphetamine]].
Cyclazodone had no documented history of recreational human usage prior to its appearance on the online research chemical market in 2017. Considering similar compounds, it is speculated that it may possess hepatotoxic and other yet-to-be-discovered toxic properties.
Cyclazodone has no documented history of recreational human usage before it appeared on the online research chemical market in 2017. Based on related compounds, it is speculated that it likely possesses hepatotoxic and other not-yet-known toxic properties. It is strongly advised to use [[responsible drug use|harm reduction practices]] if using this substance.
It is strongly advised to use [[responsible drug use|harm reduction practices]] if using this substance.
==Chemistry==
==Chemistry==
Cyclazodone is a phenyl 4-oxazolidinone that differs from the parent [[pemoline]] by an N-cyclopropyl group. Compounds like cyclazodone of the 4-oxazolidinone class can be considered as 4-oxy derivatives of the 2-amino-5-aryloxazoline class including [[aminorex]], [[fluminorex]], and [[4-methylaminorex]], conformationally restricted analogues of [[phenethylamines]] and [[amphetamines]]. Cyclazodone is structurally most closely related, not to pemoline, but rather to two N-substituted derivatives of pemoline — [[fenozolone]] (N-ethyl pemoline) and [[thozalinone]] (N,N-dimethyl pemoline).
Cyclazodone is a phenyl 4-oxazolidinone that differs from the parent [[pemoline]] by an N-cyclopropyl group. Compounds like cyclazodone of the 4-oxazolidinone class can be considered as 4-oxy derivatives of the 2-amino-5-aryloxazoline class including [[aminorex]], [[fluminorex]], and [[4-methylaminorex]], conformationally restricted analogues of [[phenethylamines]] and [[amphetamines]].
Cyclazodone is structurally most closely related, not to pemoline, but rather to two N-substituted derivatives of pemoline — [[fenozolone]] (N-ethyl pemoline) and [[thozalinone]] (N,N-dimethyl pemoline).
==Pharmacology==
==Pharmacology==
Cyclazodone is an approximately 3x - 5x more potent N-cyclopropyl derivative of [[pemoline]]. Pemoline is considered to be [[dopamine|dopaminergic]], but its precise method of action has not been fully determined.<ref>"Cylert (Pemoline)" (PDF). FDA. December 2002.</ref> Pemoline has minimal affinity for [[noradrenaline]] receptors and thus has minimal sympathomimetic side effects compared with typical dopaminergic central nervous system stimulants such as methylphenidate and [[Isomer|dextro]]-amphetamine.
Cyclazodone is an approximately 3x - 5x more potent N-cyclopropyl derivative of [[pemoline]]. Pemoline is considered to be [[dopamine|dopaminergic]], but its precise method of action has not been fully determined.<ref>"Cylert (Pemoline)" (PDF). FDA. December 2002.</ref> Pemoline has minimal affinity for [[noradrenaline]] receptors and thus has minimal sympathomimetic side effects compared with typical dopaminergic central nervous system stimulants such as methylphenidate and [[Isomer|dextro]]-amphetamine.
According to patents filed by the inventors, cyclazodone exhibited central nervous system stimulating properties and anorexigenic properties much more potent than those of pemoline, and more potent than those of various other N-lower-alkyl-substituted pemoline derivatives. At the time cyclazodone also offered a much more favorable therapeutic index and margin of safety than pemoline and other N-lower-alkyl-substituted pemoline derivatives.<ref>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent US3609159. 28 Sept. 1971.</ref>
According to patents filed by the inventors, cyclazodone exhibited central nervous system stimulating properties and anorexigenic properties more potent than that of pemoline and various other N-lower-alkyl-substituted pemoline derivatives. At the time cyclazodone also offered a much more favorable therapeutic index and margin of safety than pemoline and other N-lower-alkyl-substituted pemoline derivatives.<ref name="GuidicelliPatent">{{Citation | vauthors=((Guidicelli, D. P. R. L.)), ((Najer, H.)) | title=5-phenyl-2-cyclopropylamino-4-oxazolinone, and process for making the same | url=https://patents.google.com/patent/US3609159A/en}}</ref>
In animal models, cyclazodone exhibits central nervous system stimulant and antidepressant efficacy and potency at least equal to that of [[Isomer|dextro]]-amphetamine. The duration of maximum activity spanned 180 minutes, and the total duration of excitation was in excess of 6 hours.<ref>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent US3609159. 28 Sept. 1971.</ref> Furthermore, according to the inventor's patents, cyclazodone also possessed anorexic efficacy and potency at least equal to that of [[Isomer|dextro]]-amphetamine in animal models, yet the toxicity of cyclazodone was found to be low in comparison with the activity thereof.<ref>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent GB1005738A. 29 Sept. 1965.</ref>
In animal models, cyclazodone exhibits central nervous system stimulant and antidepressant efficacy and potency at least equal to that of [[Isomer|dextro]]-amphetamine. The duration of maximum activity spanned 180 minutes, and the total duration of excitation was in excess of 6 hours.<ref name="GuidicelliPatent" /> Furthermore, according to the inventor's patents, cyclazodone also possessed anorexic efficacy and potency at least equal to that of [[Isomer|dextro]]-amphetamine in animal models, yet the toxicity of cyclazodone was found to be low in comparison with the activity thereof.<ref name="GuidicelliPatent" />
===Pharmacodynamics===
===Pharmacodynamics===
Cyclazodone is an [[amphetamine]]-like [[agonist]] of the Trace Amine Associated Receptor 1 (TAAR1), which is a key regulator of common and trace brain monoamines such as [[dopamine]], [[serotonin]] and [[noradrenaline]].<ref>The Emerging Role of Trace Amine Associated Receptor 1 in the Functional Regulation of Monoamine Transporters and Dopaminergic Activity (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3005101/</ref><ref>Drug banks amphetamine targets | http://www.drugbank.ca/drugs/DB00182#targets</ref><ref>TA1 receptor | http://www.iuphar-db.org/DATABASE/ObjectDisplayForward?objectId=364</ref> The agonism of this set of receptors results in the release of increased concentrations of [[dopamine]], [[serotonin]] and [[noradrenaline]] in the [[synaptic cleft]]. This leads to [[Thought acceleration|cognitive]] and [[Stimulation|physical stimulation]] within the user.
Cyclazodone is likely an [[amphetamine]]-like [[agonist]] of the Trace Amine Associated Receptor 1 (TAAR1), which is a key regulator of common and trace brain monoamines such as [[dopamine]], [[serotonin]] and [[noradrenaline]].<ref>{{cite journal | vauthors=((Miller, G. M.)) | journal=Journal of neurochemistry | title=The Emerging Role of Trace Amine Associated Receptor 1 in the Functional Regulation of Monoamine Transporters and Dopaminergic Activity | volume=116 | issue=2 | pages=164–176 | date= January 2011 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3005101/ | issn=0022-3042 | doi=10.1111/j.1471-4159.2010.07109.x}}</ref><ref>{{Citation | title=Amphetamine | url=https://go.drugbank.com/drugs#targets}}</ref><ref>TA1 receptor | http://www.iuphar-db.org/DATABASE/ObjectDisplayForward?objectId=364</ref> The agonism of this set of receptors results in the release of increased concentrations of [[dopamine]], [[serotonin]] and [[noradrenaline]] in the [[synaptic cleft]]. This leads to [[Thought acceleration|cognitive]] and [[Stimulation|physical stimulation]] within the user.
==Subjective effects==
==Subjective effects==
The effects of cyclazodone have been compared to those of [[amphetamine]], but with the addition of a low to moderate affinity for [[serotonin]] release comparable to that of [[methamphetamine]] and [[3-FMA]].
The stimulant effects of cyclazodone have been compared to those of [[amphetamine]], but with the addition of a low to moderate affinity for [[serotonin]] release comparable to that of [[methamphetamine]] and [[3-FMA]]. Additionally, it is noticeably less euphoric than amphetamine and appears to have less sympathomimetic activation.
Some anecdotal reports suggest that [[cyclazodone]] and its parent compound [[pemoline]] might exhibit nootropic or cognitive enhancement characteristics, potentially additional to or unique from those associated with typical dopaminergic central nervous system stimulants such as [[methylphenidate]] and [[amphetamine]].
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
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|{{effects/physical|
|{{effects/physical|
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, cyclazodone is usually considered to be somewhat stimulating though soft in a fashion that is slightly weaker to that of [[methamphetamine]], but stronger than that of [[modafinil]], [[caffeine]], and [[methylphenidate]]. An elevated heart rate more than that of [[amphetamine]] is often reported.
*'''[[Effect::Stimulation]]''' - Cyclazodone is reported to be somewhat stimulating though soft in a fashion that is slightly weaker to that of [[methamphetamine]], but stronger than that of [[modafinil]], [[caffeine]], and [[methylphenidate]].
*'''[[Effect::Physical euphoria]]''' - This effect is dose dependent and tends only to be present at higher doses. Cyclazodone is reported to lack the body glow associated with [[amphetamine]] at typical doses.
*'''[[Effect::Physical euphoria]]''' - This effect is dose dependent and tends only to be present at higher doses. Cyclazodone is reported to lack the body glow associated with [[amphetamine]] at typical doses.
*'''[[Effect::Nausea]]''' - Typically a result of dosing for prolonged periods of time and dehydration.
*'''[[Effect::Pain relief]]'''
*'''[[Effect::Pupil dilation]]''' - This effect is typically experienced only at higher dosages and is more prominent on the comedown.
*'''[[Effect::Pupil dilation]]''' - This effect is typically experienced only at higher dosages and is more prominent on the comedown.
*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]].
*'''[[Effect::Teeth grinding]]''' - This component is reported to be less intense compared to[[MDMA]], and only prominent when dosing for prolonged periods of time.
*'''[[Effect::Anxiety]]''' & '''[[Effect::Paranoia]]''' - This effect is dose dependent and typically occurs with overly high doses or after redosing and staying awake for extended periods of time.
*'''[[Effect::Anxiety]]''' & '''[[Effect::Paranoia]]''' - This effect is dose dependent and typically occurs with overly high doses or after redosing and staying awake for extended periods of time.
*'''[[Effect::Anxiety suppression]]''' - Normal to moderately high doses will tend to result in a loss of anxiety.
*'''[[Effect::Anxiety suppression]]''' - Common to moderately high doses, when used infrequently, will tend to result in a complete loss of all anxiety symptoms.
*'''[[Effect::Cognitive euphoria]]''' - This effect is dose dependent; a low dose will tend to produce only that of a slight mood lift and moderate to high doses are typically reported to be on par with that of [[amphetamine]] though less than that of [[methamphetamine]], [[3-FMA]], and [[4-methylaminorex]].
*'''[[Effect::Cognitive euphoria]]''' - This effect is dose dependent; a low dose will tend to produce only that of a slight mood lift and moderate to high doses are typically reported to be on par with that of [[amphetamine]] though less than that of [[methamphetamine]], [[3-FMA]], and [[4-methylaminorex]]. It is the strongest when used infrequently at moderate doses, and binges often result in a loss of this effect.
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - Cyclazodone has been reported to produce moderate prosocial and entactogenic effects which, although much weaker than that of traditional entactogens such as [[MDMA]], are still prominent and slightly surpassing that of [[amphetamine]]. As with most amphetamine-like stimulants this effect tends to rapidly fade with prolonged use.
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - Cyclazodone has been reported to produce moderately strong prosocial and entactogenic effects which, although much weaker than that of traditional entactogens such as [[MDMA]], surpass that of [[amphetamine]]. As with most amphetamine-like stimulants, this effect rapidly fades with prolonged use.
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Delusion]]'''
*'''[[Effect::Delusion]]'''
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Ego inflation]]'''
*'''[[Effect::Ego inflation]]''' - Cyclazodone, at moderate doses, has been reported to substantially increase confidence and self-esteem. Higher doses, however, can result in complete self-absorption and ego mania.
*'''[[Effect::Emotion suppression]]
*'''[[Effect::Emotion suppression]]
*'''[[Effect::Focus enhancement]]'''
*'''[[Effect::Focus enhancement]]'''
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*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Muscle cramps]]'''
*'''[[Effect::Tactile hallucinations]]'''
}}
}}
}}
}}
===Experience reports===
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]].
There are currently {{#ask:[[Category:Cyclazodone]][[Category:Experience]] | format=count}} experience reports which describe the effects of this substance in our [[experience index]].
The toxicity and long-term health effects of recreational cyclazodone use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]]. This is because cyclazodone has a very limited history of human usage.
The toxicity and long-term health effects of recreational cyclazodone use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]]. This is because cyclazodone has a very limited history of human usage.
Another compound related in structure, [[4-methylaminorex]], is associated with pulmonary hypertension<ref>https://www.ncbi.nlm.nih.gov/pubmed/11083709</ref>; though, it is reported to induce far stronger stimulation than that of cyclazodone.
Another compound related in structure, [[4-methylaminorex]], is associated with pulmonary hypertension<ref>{{cite journal | vauthors=((Gaine, S. P.)), ((Rubin, L. J.)), ((Kmetzo, J. J.)), ((Palevsky, H. I.)), ((Traill, T. A.)) | journal=Chest | title=Recreational use of aminorex and pulmonary hypertension | volume=118 | issue=5 | pages=1496–1497 | date= November 2000 | issn=0012-3692 | doi=10.1378/chest.118.5.1496}}</ref>; though, it is reported to induce far stronger stimulation than that of cyclazodone.
The structurally related compound pemoline was removed from the market after it was found to cause liver damage in children.<ref>Marotta, P. J., & Roberts, E. A. (1998). Pemoline hepatotoxicity in children. The Journal of Pediatrics, 132(5), 894-897.</ref>
The structurally related compound pemoline was removed from the market after it was found to cause liver damage in children.<ref>{{cite journal | vauthors=((Marotta, P. J.)), ((Roberts, E. A.)) | journal=The Journal of Pediatrics | title=Pemoline hepatotoxicity in children | volume=132 | issue=5 | pages=894–897 | date= May 1998 | url=https://linkinghub.elsevier.com/retrieve/pii/S0022347698703294 | issn=00223476 | doi=10.1016/S0022-3476(98)70329-4}}</ref>
In rodents and primates, sufficiently high doses of monoamine [[releasing agent|releasing agents]] cause dopaminergic neurotoxicity, or damage to dopamine neurons, which is characterized by reduced transporter and receptor function. There is no evidence that [[releasing agent]]s are directly neurotoxic in humans. However, large doses of [[releasing agent]]s may cause indirect neurotoxicity as a result of increased oxidative stress from reactive oxygen species and autoxidation of dopamine.{{citation needed}}
In rodents and primates, sufficiently high doses of monoamine [[releasing agent|releasing agents]] cause dopaminergic neurotoxicity, or damage to dopamine neurons, which is characterized by reduced transporter and receptor function. There is no evidence that [[releasing agent]]s are directly neurotoxic in humans. However, large doses of [[releasing agent]]s may cause indirect neurotoxicity as a result of increased oxidative stress from reactive oxygen species and autoxidation of dopamine.{{citation needed}}
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Addiction is a serious risk with heavy recreational stimulant use but is unlikely to arise from typical long-term medical use at therapeutic doses. Notably, the structurally related compound pemoline fails to demonstrate a potential for self-administration in primates and is considered to have reduced risk of dependence relative to those more typical dopaminergic stimulants. Caution is nonetheless advised, as with other monoamine [[releasing agent]]s.
Addiction is a serious risk with heavy recreational stimulant use but is unlikely to arise from typical long-term medical use at therapeutic doses. Notably, the structurally related compound pemoline fails to demonstrate a potential for self-administration in primates and is considered to have reduced risk of dependence relative to those more typical dopaminergic stimulants. Caution is nonetheless advised, as with other monoamine [[releasing agent]]s.
Tolerance to many of the effects of cyclazodone [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Cyclazodone presents [[Cross-tolerance::all [[dopamine]]rgic [[stimulant]]s]], meaning that after the consumption of amphetamine all [[stimulant]]s will have a reduced effect.
Tolerance to many of the effects of cyclazodone [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Cyclazodone presents cross-tolerance with [[Cross-tolerance::all [[dopamine]]rgic [[stimulant]]s]], meaning that after the consumption of cyclazodone all [[stimulant]]s will have a reduced effect.
===Psychosis===
===Psychosis===
{{Main|Stimulant psychosis}}
{{Main|Stimulant psychosis}}
Based on its pharmacological similarity to other stimulants, it is likely that misuse of this compound can result in state of psychosis marked by a variety of symptoms (e.g., [[Paranoia|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref>http://www.drugabuse.gov/drugs-abuse/emerging-trends</ref><ref name="amppsychosis">Shoptaw, S. J., Kao, U., & Ling, W. (2009). Treatment for amphetamine psychosis. The Cochrane Library.</ref> A review on the treatment for [[amphetamine]] and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref name="amppsychosis" /><ref>Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.</ref> The same review asserts that based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref name="amppsychosis" /> Psychosis very rarely arises from therapeutic use. The combination of the prolonged use of high doses combined with sleep deprivation significantly increases the risk of stimulant psychosis.{{citation needed}}
Based on its pharmacological similarity to other stimulants, it is likely that misuse of this compound can result in state of psychosis marked by a variety of symptoms (e.g., [[Paranoia|paranoia]], [[External hallucinations|hallucinations]], or [[Delusions|delusions]]).<ref>{{Citation | vauthors=((National Institute on Drug Abuse)) | title=Emerging Trends | url=https://nida.nih.gov/research-topics/emerging-trends-alerts}}</ref><ref name="amppsychosis">{{cite book | vauthors=((Shoptaw, S. J.)), ((Kao, U.)), ((Ling, W. W.)) | veditors=((The Cochrane Collaboration)) | date=8 October 2008 | chapter=The Cochrane Database of Systematic Reviews (Complete Reviews) | title=Treatment for amphetamine psychosis | publisher=John Wiley & Sons, Ltd | pages=CD003026.pub2 | url=https://doi.wiley.com/10.1002/14651858.CD003026.pub2 | doi=10.1002/14651858.CD003026.pub2}}</ref> A review on the treatment for [[amphetamine]] and [[methamphetamine]] abuse-induced psychosis states that about 5–15% of users fail to recover completely.<ref name="amppsychosis" /><ref>{{cite book | vauthors=((Hofmann, F. G.)) | date= 1983 | title=A handbook on drug and alcohol abuse: the biomedical aspects | publisher=Oxford University Press | edition=2nd ed | isbn=9780195030563}}</ref> The same review asserts that based upon at least one trial, [[antipsychotic]] medications effectively resolve the symptoms of acute amphetamine psychosis.<ref name="amppsychosis" /> Psychosis very rarely arises from therapeutic use. The combination of the prolonged use of high doses combined with sleep deprivation significantly increases the risk of stimulant psychosis.{{citation needed}}
===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
*'''[[Stimulants]]''' - Cyclazodone can be potentially dangerous in combination with other [[stimulant]]s as it can [[increased heart rate|increase one's heart rate]] and [[increased blood pressure|blood pressure]] to dangerous levels.
{{DangerousInteractions/Stimulants}}
*'''[https://en.wikipedia.org/wiki/Tricyclic_antidepressant Tricyclic antidepressants]''' - Cyclazodone may increase the effects of tricyclic antidepressants to dangerous levels.<ref>Adderall Prescription info | http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf</ref>
*'''[[MDMA]]''' - The neurotoxic effects of [[MDMA]] may be increased when combined with other amphetamine-like stimulants.
{{DangerousInteractions/MAOI|nt=dopamine}}
*'''[[Cocaine]]''' - This combination may increase strain on the heart to dangerous levels.
==Legal status==
==Legal status==
Cyclazodone is currently a gray area compound within all parts of the world, meaning its regulation lies in a legal gray area and that it is not known to be specifically illegal (''"scheduled"'') within any country. However, people may still be charged for its possession under certain circumstances such as under analogue laws and with intent to sell or consume. It is a banned stimulant under the World Anti-Doping Agency prohibited list.
Cyclazodone is currently a gray area compound within all parts of the world, meaning its regulation lies in a legal gray area and that it is not known to be specifically illegal (''"scheduled"'') within any country. However, people may still be charged for its possession under certain circumstances such as under analogue laws and with intent to sell or consume. It is a banned stimulant under the World Anti-Doping Agency prohibited list.
* '''United States:''' Cyclazodone being an analogue of [[pemoline]], a Schedule IV controlled substance in the US, may fall under Federal Analogue Act, 21 U.S.C. § 813<ref>https://www.law.cornell.edu/uscode/text/21/813</ref> when intended for human consumption.
*'''Germany''': Cyclazodone is not a controlled substance under the BtMG (''Narcotics Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/BJNR106810981.html|title=Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG)|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 28, 2019|language=de}}</ref> or the NpSG (''New Psychoactive Substances Act'').<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/BJNR261510016.html|title=Neue-psychoaktive-Stoffe-Gesetz (NpSG)|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 28, 2019|language=de}}</ref> According to §2 AMG (''Medicines Act'') it would fall under the definition of a medicine because it induces pharmacological effect.<ref>{{cite web|url=https://www.gesetze-im-internet.de/amg_1976/__2.html|title=§ 2 AMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 28, 2019|language=de}}</ref> By a decision of the European Court of Justice, this definition was declared ineffective because it was not compatible with EU law.<ref>{{cite news|url=https://www.lto.de/recht/hintergruende/h/eugh-urteil-c35813-c18114-legal-highs-kein-arzneimittel-strafbar-amg-btmg/|title= Cannabinoide Kräutermischungen vor dem EuGH: Legal Highs bleiben legal|publisher=LTO|author=Prof. Dr. Helmut Pollähne|trans-title=Cannabinoid herbal mixtures at the ECJ: Legal highs stay legal|date=July 11, 2014|access-date=December 28, 2019|language=de}}</ref> Cyclazodone can be considered legal.
*'''Switzerland''': Cyclazodone is not controlled under Buchstabe A, B, C and D. It could be considered legal.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''United States''': Cyclazodone being an analogue of [[pemoline]], a Schedule IV controlled substance in the US, may fall under Federal Analogue Act, 21 U.S.C. § 813<ref>{{Citation | title=21 U.S. Code § 813 - Treatment of controlled substance analogues | url=https://www.law.cornell.edu/uscode/text/21/813}}</ref> when intended for human consumption.
* Segal, D. S., Cox Jr, R. H., Stern, W. C., & Maickel, R. P. (1967). Stimulatory effects of pemoline and cyclopropylpemoline on continuous avoidance behavior: similarity to effects of D-amphetamine. Life Sciences, 6(23), 2567-2572. https://doi.org/10.1016/0024-3205(67)90322-0
*Segal, D. S., Cox Jr, R. H., Stern, W. C., & Maickel, R. P. (1967). Stimulatory effects of pemoline and cyclopropylpemoline on continuous avoidance behavior: similarity to effects of D-amphetamine. Life Sciences, 6(23), 2567-2572. https://doi.org/10.1016/0024-3205(67)90322-0
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
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.
Cyclazodone was developed in the 1960s by the American Cyanamid Company. Its non-clinical use has only found recent attention as a research chemical study aid. It should be noted that the lack of pharmacological data and extremely limited history of human usage pose considerable concern regarding its long-term use as a substitute for prescription stimulants.
Cyclazodone had no documented history of recreational human usage prior to its appearance on the online research chemical market in 2017. Considering similar compounds, it is speculated that it may possess hepatotoxic and other yet-to-be-discovered toxic properties.
Cyclazodone is a phenyl 4-oxazolidinone that differs from the parent pemoline by an N-cyclopropyl group. Compounds like cyclazodone of the 4-oxazolidinone class can be considered as 4-oxy derivatives of the 2-amino-5-aryloxazoline class including aminorex, fluminorex, and 4-methylaminorex, conformationally restricted analogues of phenethylamines and amphetamines.
Cyclazodone is structurally most closely related, not to pemoline, but rather to two N-substituted derivatives of pemoline — fenozolone (N-ethyl pemoline) and thozalinone (N,N-dimethyl pemoline).
Pharmacology
Cyclazodone is an approximately 3x - 5x more potent N-cyclopropyl derivative of pemoline. Pemoline is considered to be dopaminergic, but its precise method of action has not been fully determined.[1] Pemoline has minimal affinity for noradrenaline receptors and thus has minimal sympathomimetic side effects compared with typical dopaminergic central nervous system stimulants such as methylphenidate and dextro-amphetamine.
According to patents filed by the inventors, cyclazodone exhibited central nervous system stimulating properties and anorexigenic properties more potent than that of pemoline and various other N-lower-alkyl-substituted pemoline derivatives. At the time cyclazodone also offered a much more favorable therapeutic index and margin of safety than pemoline and other N-lower-alkyl-substituted pemoline derivatives.[2]
In animal models, cyclazodone exhibits central nervous system stimulant and antidepressant efficacy and potency at least equal to that of dextro-amphetamine. The duration of maximum activity spanned 180 minutes, and the total duration of excitation was in excess of 6 hours.[2] Furthermore, according to the inventor's patents, cyclazodone also possessed anorexic efficacy and potency at least equal to that of dextro-amphetamine in animal models, yet the toxicity of cyclazodone was found to be low in comparison with the activity thereof.[2]
The stimulant effects of cyclazodone have been compared to those of amphetamine, but with the addition of a low to moderate affinity for serotonin release comparable to that of methamphetamine and 3-FMA. Additionally, it is noticeably less euphoric than amphetamine and appears to have less sympathomimetic activation.
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 PsychonautWikicontributors. 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 euphoria - This effect is dose dependent and tends only to be present at higher doses. Cyclazodone is reported to lack the body glow associated with amphetamine at typical doses.
The visual effects of cyclazodone are usually less consistent and only mildly noticeable at higher dosages. They may manifest as a brightening of colors and areas of light appearing brighter than that of their surrounding.
Distortions
Drifting(breathing and morphing) - This effect is usually subtle and barely noticeable and only occurs at higher dosages or when combined with cannabis.
Brightness alteration - Cyclazodone can make spaces seem brighter as a result of its pupil dilating effects.
Hallucinatory states
Transformations - This effect occurs very rarely, and typically only when the user has taken high doses, is coming down, or has been awake for unusually long periods. It is usually very mild when it does occur.
Anxiety & Paranoia - This effect is dose dependent and typically occurs with overly high doses or after redosing and staying awake for extended periods of time.
Anxiety suppression - Common to moderately high doses, when used infrequently, will tend to result in a complete loss of all anxiety symptoms.
Cognitive euphoria - This effect is dose dependent; a low dose will tend to produce only that of a slight mood lift and moderate to high doses are typically reported to be on par with that of amphetamine though less than that of methamphetamine, 3-FMA, and 4-methylaminorex. It is the strongest when used infrequently at moderate doses, and binges often result in a loss of this effect.
Empathy, affection, and sociability enhancement - Cyclazodone has been reported to produce moderately strong prosocial and entactogenic effects which, although much weaker than that of traditional entactogens such as MDMA, surpass that of amphetamine. As with most amphetamine-like stimulants, this effect rapidly fades with prolonged use.
Ego inflation - Cyclazodone, at moderate doses, has been reported to substantially increase confidence and self-esteem. Higher doses, however, can result in complete self-absorption and ego mania.
Time distortion - This can be described as the experience of time speeding up and passing much quicker than it usually would when sober.
After effects
The effects which occur during the offset of a stimulant experience generally feel negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and occurs because of neurotransmitter depletion. Its effects commonly include:
There are currently 0 experience reports which describe the effects of this substance in our experience index.
Toxicity and harm potential
The toxicity and long-term health effects of recreational cyclazodone use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because cyclazodone has a very limited history of human usage.
Another compound related in structure, 4-methylaminorex, is associated with pulmonary hypertension[6]; though, it is reported to induce far stronger stimulation than that of cyclazodone.
The structurally related compound pemoline was removed from the market after it was found to cause liver damage in children.[7]
In rodents and primates, sufficiently high doses of monoamine releasing agents cause dopaminergic neurotoxicity, or damage to dopamine neurons, which is characterized by reduced transporter and receptor function. There is no evidence that releasing agents are directly neurotoxic in humans. However, large doses of releasing agents may cause indirect neurotoxicity as a result of increased oxidative stress from reactive oxygen species and autoxidation of dopamine.[citation needed]
Addiction is a serious risk with heavy recreational stimulant use but is unlikely to arise from typical long-term medical use at therapeutic doses. Notably, the structurally related compound pemoline fails to demonstrate a potential for self-administration in primates and is considered to have reduced risk of dependence relative to those more typical dopaminergic stimulants. Caution is nonetheless advised, as with other monoamine releasing agents.
Tolerance to many of the effects of cyclazodone develops with prolonged and repeated use. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about 3 - 7 days for the tolerance to be reduced to half and 1 - 2 weeks to be back at baseline (in the absence of further consumption). Cyclazodone presents cross-tolerance with [[Cross-tolerance::all dopaminergicstimulants]], meaning that after the consumption of cyclazodone all stimulants will have a reduced effect.
Based on its pharmacological similarity to other stimulants, it is likely that misuse of this compound can result in state of psychosis marked by a variety of symptoms (e.g., paranoia, hallucinations, or delusions).[8][9] A review on the treatment for amphetamine and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely.[9][10] The same review asserts that based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.[9] Psychosis very rarely arises from therapeutic use. The combination of the prolonged use of high doses combined with sleep deprivation significantly increases the risk of stimulant psychosis.[citation needed]
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.
"[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] & "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 25x compounds are highly stimulating and physically straining. Combinations with Cyclazodone should be strictly avoided due to the risk of excessive stimulation and heart strain. This can result in increased blood pressure, vasoconstriction, panic attacks, thought loops, seizures, and heart failure in extreme cases.
"[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Combining alcohol with stimulants can be dangerous due to the risk of accidental over-intoxication. Stimulants mask alcohol's depressant effects, which is what most people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects will be left unopposed, which can result in blackouts and severe respiratory depression. If mixing, the user should strictly limit themselves to only drinking a certain amount of alcohol per hour.
"[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Combinations with DXM should be avoided due to its inhibiting effects on serotonin and norepinephrine reuptake. There is an increased risk of panic attacks and hypertensive crisis, or serotonin syndrome with serotonin releasers (MDMA, methylone, mephedrone, etc.). Monitor blood pressure carefully and avoid strenuous physical activity.
"[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Any neurotoxic effects of MDMA are likely to be increased when other stimulants are present. There is also a risk of excessive blood pressure and heart strain (cardiotoxicity).
"[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
"[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
"[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Cyclazodone may be dangerous to combine with other stimulants like cocaine as they can increase one's heart rate and blood pressure to dangerous levels.
"[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is known to lower the seizure threshold[11] and combinations with stimulants may further increase this risk.
Legal status
Cyclazodone is currently a gray area compound within all parts of the world, meaning its regulation lies in a legal gray area and that it is not known to be specifically illegal ("scheduled") within any country. However, people may still be charged for its possession under certain circumstances such as under analogue laws and with intent to sell or consume. It is a banned stimulant under the World Anti-Doping Agency prohibited list.
Germany: Cyclazodone is not a controlled substance under the BtMG (Narcotics Act)[12] or the NpSG (New Psychoactive Substances Act).[13] According to §2 AMG (Medicines Act) it would fall under the definition of a medicine because it induces pharmacological effect.[14] By a decision of the European Court of Justice, this definition was declared ineffective because it was not compatible with EU law.[15] Cyclazodone can be considered legal.
Switzerland: Cyclazodone is not controlled under Buchstabe A, B, C and D. It could be considered legal.[16]
United States: Cyclazodone being an analogue of pemoline, a Schedule IV controlled substance in the US, may fall under Federal Analogue Act, 21 U.S.C. § 813[17] when intended for human consumption.
Segal, D. S., Cox Jr, R. H., Stern, W. C., & Maickel, R. P. (1967). Stimulatory effects of pemoline and cyclopropylpemoline on continuous avoidance behavior: similarity to effects of D-amphetamine. Life Sciences, 6(23), 2567-2572. https://doi.org/10.1016/0024-3205(67)90322-0
↑Gaine, S. P., Rubin, L. J., Kmetzo, J. J., Palevsky, H. I., Traill, T. A. (November 2000). "Recreational use of aminorex and pulmonary hypertension". Chest. 118 (5): 1496–1497. doi:10.1378/chest.118.5.1496. ISSN0012-3692.
↑Hofmann, F. G. (1983). A handbook on drug and alcohol abuse: the biomedical aspects (2nd ed ed.). Oxford University Press. ISBN9780195030563.CS1 maint: Extra text (link)
↑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. eISSN1937-6995. ISSN1556-9039. OCLC163567183.
