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Cyclazodone: Difference between revisions
>Scrumptious m Correction of the stated potency, which was in reference to fenozolone (2-monoethylamino), not pemoline, and adjustment of the wording |
>Scrumptious Added some additional information, and updated wording! |
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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]]. | '''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]]. Its mechanism of action involves promoting the release of [[dopamine]] and [[norepinephrine]] in the brain. | ||
Cyclazodone was developed | Cyclazodone was developed by the American Cyanamid Company in the 1960s for use as an appetite suppressant and an antidepressant. Its non-clinical use has only found recent attention as a [[research chemical]] study aid. The lack of pharmacological data and limited human usage history raise concerns about its long-term use as a stimulant substitute. | ||
[[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]]. | [[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. | Cyclazodone had no documented history of recreational human usage prior to its appearance on the online research chemical market in 2017. However, discussions about it on various forums date back as early as 2002<ref>[https://www.thevespiary.org/talk/index.php?topic=11491.0 "Fenozolone - a different stimulant."] The Vespiary. (2002).</ref>. Concerns persist about potential hepatotoxic and other yet-to-be-discovered toxic properties, but there have been no reported cases of hepatotoxicity attributed to cyclazodone thus far. | ||
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. | ||
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==Pharmacology== | ==Pharmacology== | ||
Cyclazodone is a more potent N-cyclopropyl derivative of [[pemoline]]. Pemoline is considered to be [[dopamine|dopaminergic]], | Cyclazodone is a more potent N-cyclopropyl derivative of [[pemoline]]. Pemoline is considered to be [[dopamine|dopaminergic]], yet its precise mechanism of action remained elusive during its market presence.<ref>"Cylert (Pemoline)" (PDF). FDA. December 2002.</ref> | ||
According to | Pemoline's mild sympathomimetic side effects and weaker anorectic effects suggest limited affinity for [[noradrenaline]] and potentially [[serotonin]] receptors compared to other central nervous system stimulants. This characteristic appears to be shared with cyclazodone, as demonstrated by the limited sympathomimetic effects observed in dogs following administration, , evidenced by limited sympathomimetic effects observed in dogs following administration. | ||
According to the patent filed by the inventors, cyclazodone demonstrated significant central nervous system stimulation and antidepressant properties, and relative potency greater than both 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 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" /> | 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" /> | ||
The related compound [[N-Methyl-Cyclazodone]] seems to function as a pro-drug for cyclazodone, leading to the presence of significant amounts of cyclazodone in urine after consumption.<ref name=":0">Basile, J., Nolan, J., Krotulski, A. J., Osterhoudt, K. (April 25, 2022). [https://www.cfsre.org/resources/presentations/toxicity-from-the-nps-n-methyl-cyclazodone-with-laboratory-confirmation-a-dance-befitting-st-vitus "Toxicity from the NPS N-Methyl-Cyclazodone with Laboratory Confirmation - A Dance Befitting St. Vitus."] Presentation at the American Academy of Clinical Toxicology- 2022 Conference Meeting.</ref> | |||
===Pharmacodynamics=== | ===Pharmacodynamics=== | ||
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==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
The | The 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. | ||
One adult presented with moderate intoxication after the consumption of 5,000 mg of [[N-Methyl-Cyclazodone]] over the course of five days. [[N-Methyl-Cyclazodone]] appears to act as a pro-drug for cyclazodone, with detectable levels found in urine, as detailed in the same toxicological report. <ref name=":0" /> | |||
Another compound | Another structurally related compound, [[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 withdrawn from the market due to its | The structurally related compound [[pemoline]] was withdrawn from the market in 2005 due to concerns about its potential to cause spontaneous serious 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}} | ||
Cyclazodone has demonstrated LD50 values of 81 mg/kg (intraperitoneal) and 142 mg/kg (subcutaneous) in rats. | |||
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | ||
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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 with [[Cross-tolerance::all [[dopamine]]rgic [[stimulant]]s]], meaning that after the consumption of cyclazodone all [[stimulant]]s | Tolerance to many of the effects of cyclazodone [[Time to full tolerance::develops with prolonged and repeated use|tends to develop with prolonged or repeated use::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 may have a reduced effect. | ||
===Psychosis=== | ===Psychosis=== | ||
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*'''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> | *'''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. | *'''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. | ||
*'''Sweden''': Cyclazodone is not a classified or controlled substance in Sweden. However, the related compound N-Methyl-Cyclazodone was subject to investigation in Sweden in 2018. Despite this, authorities chose not to proceed with classification, ultimately resulting in the discontinuation of the investigation, and it has remained legal. <ref>[https://www.folkhalsomyndigheten.se/contentassets/bcdb559206774cd4a6bc842c233bd318/02384-2018.pdf Folkhälsomyndigheten - N-Metyl-Cyklazodon]</ref> | |||
==See also== | ==See also== | ||