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| Summary sheet: N-Methyl-Cyclazodone |
| N-Methyl-Cyclazodone | |||||||||||||||||||||||||||||||
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||
| Common names | N-Methyl-Cyclazodone, N-Cyclopropyl-N-Methylpemoline, NMC | ||||||||||||||||||||||||||||||
| Substitutive name | N-Methyl-Cyclazodone | ||||||||||||||||||||||||||||||
| Systematic name | 2-(Cyclopropyl(methyl)amino)-5-phenyl-1,3-oxazol-4-one | ||||||||||||||||||||||||||||||
| Class Membership | |||||||||||||||||||||||||||||||
| Psychoactive class | Stimulant | ||||||||||||||||||||||||||||||
| Chemical class | Substituted aminorexes | ||||||||||||||||||||||||||||||
| Routes of Administration | |||||||||||||||||||||||||||||||
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N-Cyclopropyl-N-Methylpemoline (also known as N-Methyl-Cyclazodone or NMC) is a novel stimulant substance of the 4-oxazolidinone class. is structurally related to thozalinone and cyclazodone. Similar to amphetamine, the addition of the methyl group on cyclazodone is thought to increase its potency and duration. The mechanism of action involves promoting the release of dopamine, norepinephrine, and serotonin in the brain.
Unlike cyclazodone, N-methyl-cyclazodone has little to no history of use and only recently emerged as a study aid. Its non-clinical use has only found recent attention as a research chemical study aid or atypical antidepressant. 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 or antidepressants. Similar to methamphetamine, this substance is reported to possess an usually long duration, it is therefore recommended to take one's dose in the morning and avoid redosing.
Subjective effects include stimulation, focus enhancement, stamina enhancement, increased blood pressure, and mild euphoria. Some anecdotal reports suggest that N-methyl-cyclazodone and its parent compound cyclazodone may have nootropic properties similar to central nervous system stimulants such as methylphenidate and amphetamine.
One of its parent compounds, thozalinone, has been used as an antidepressant in europe[1], which may be due to its serotonin-releasing properties.
N-methyl-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 harm reduction practices if using this substance.
Chemistry
N-Methyl-Cyclazodone is a phenyl 4-oxazolidinone that differs from the parent pemoline by an N-cyclopropyl and N-methyl group. Compounds like N-Methyl-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.
N-Methyl-Cyclazodone is structurally most closely related to cyclazodone and thozalinone (N,N-dimethyl pemoline).
Pharmacology
N-Methyl-Cyclazodone is an approximately 4x - 6x more potent N,N-methylcyclopropyl derivative of pemoline. Pemoline is considered to be dopaminergic, but its precise method of action has not been fully determined.[2] Pemoline has minimal affinity for noradrenaline receptors and thus has “minimal” sympathomimetic side effects, (although increased dopamine release is thought to cause an increse in more the release of norepinephrine thereby cussing sympathomimetic effects)
Subjective effects
The effects of N-methyl-cyclazodone could be compared to those of cyclazodone and modafinil, but with longer duration and potentially more side effects. It also possesses mild serotonin-releasing properties comparable to that of methamphetamine and 3-FMA, which become more prominent at higher doses, accompanied with greater side effects. Additionally, it is noticeably less euphoric than methamphetamine and 3-FMA 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 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 
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- Stimulation - N-methyl-cyclazodone is reported to be somewhat stimulating though soft in a fashion that is generally weaker than methamphetamine, but stronger than modafinil, caffeine, and methylphenidate. It can encourage physical activities such as dancing, socializing, running, or cleaning. The particular style of stimulation which amphetamine produces can be described as forced.
- Physical euphoria - This effect is dose dependent and tends only to be present at higher doses. N-methyl-cyclazodone is reported to lack the body glow associated with amphetamine at typical doses.
- Stamina enhancement
- Abnormal heartbeat[citation needed]
- Increased heart rate[citation needed] - This effect is reported to be not as strong with N-methyl-cyclazodone as with cyclazodone
- Increased blood pressure[citation needed]
- Appetite suppression
- Bronchodilation
- Dehydration
- Dry mouth
- Frequent urination
- Headaches
- Increased bodily temperature
- Increased perspiration
- Nausea - Typically a result of dosing for prolonged periods of time and dehydration.
- Pupil dilation - This effect is typically experienced only at higher dosages and is more prominent on the comedown.
- Stomach cramps
- Teeth grinding - This component is reported to be less intense compared to MDMA, and only prominent when dosing for prolonged periods of time.
- Temporary erectile dysfunction
- Vasoconstriction[citation needed]
- Restless legs
- Muscle cramps
Visual effects 
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N-methyl-cyclazodone may produce mild visual effects at higher dosages and in combination with Sleep deprivation if the user has been awake for long periods of time. They are generally less common than with amphetamines.
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 - N-methyl-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.
Cognitive effects 
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- Analysis enhancement
- 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 - The anxiolytic effects of N-methyl-cyclazodone are generally weaker than those of cyclazodone.
- 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 and 3-FMA. 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 - N-methyl-cyclazodone has been reported to produce low to 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.
- Compulsive redosing - This effect is generally much less prominent than with cyclazodone mostly due its long duration.
- Delusion
- Disinhibition
- Ego inflation
- Emotion suppression
- Focus enhancement - N-methyl-cyclazodone is reported to produce strong focus-enhancing effects that rival common ADHD stimulants such as amphetamine and methylphenidate.
- Increased libido
- Increased music appreciation - This effect is usually weaker than with cyclazodone.
- Motivation enhancement
- Bodily control enhancement
- Thought acceleration
- Thought organization
- Wakefulness - This effect is reported to be similar in duration to methamphetamine, with some users reporting an inability to sleep. It is advised to take one's dose at the start of the day to minimize this effect.
- 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 
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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. The "comedown" of N-methyl-cyclazodone is generally weaker and smoother and that of cyclazodone, with some users reporting no after effects at all. Its effects commonly include:
- Anxiety
- Cognitive fatigue
- Delusion
- Depression - The after effects of N-methyl-cyclazodone are generally weaker than those of cyclazodone
- Headaches
- Irritability
- Motivation suppression
- Thought deceleration
- Wakefulness
- Muscle cramps
- Tactile hallucinations
Experience reports
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 N-methyl-cyclazodone use do not seem to have been studied in any scientific context and the exact toxic dosage is unknown. This is because N-methyl-cyclazodone has a very limited history of human usage.
Another compound related in structure, 4-methylaminorex, is associated with pulmonary hypertension[3]; though, it is reported to induce far stronger stimulation than that of N-methyl-cyclazodone.
The structurally related compound pemoline was removed from the market after it was found to cause liver damage in children.[4]
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]
It is strongly recommended that one use harm reduction practices when using this substance.
Tolerance and addiction potential
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 N-methyl-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). N-methyl-cyclazodone presents cross-tolerance with all dopaminergic stimulants, meaning that after the consumption of N-methyl-cyclazodone all stimulants will have a reduced effect.
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, hallucinations, or delusions).[5][6] A review on the treatment for amphetamine and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely.[6][7] The same review asserts that based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.[6] 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.
- 25x-NBOMe & 25x-NBOH - 25x compounds are highly stimulating and physically straining. Combinations with N-Methyl-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.
- Alcohol - 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.
- DXM - 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.
- MDMA - 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).
- MXE - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
- Dissociatives - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
- Stimulants - N-Methyl-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.
- Tramadol - Tramadol is known to lower the seizure threshold[8] and combinations with stimulants may further increase this risk.
Legal status
N-methyl-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: N-methyl-cyclazodone is not a controlled substance under the BtMG (Narcotics Act)[9] or the NpSG (New Psychoactive Substances Act).[10] According to §2 AMG (Medicines Act) it would fall under the definition of a medicine because it induces pharmacological effect.[11] By a decision of the European Court of Justice, this definition was declared ineffective because it was not compatible with EU law.[12] Cyclazodone can be considered legal.
- Switzerland: N-methyl-cyclazodone is not controlled under Buchstabe A, B, C and D. It could be considered legal.[13]
- United States: N-methyl-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[14] when intended for human consumption.
See also
External links
Literature
References
- ↑ Gallant DM, Bishop MP, Scrignar CB, Hornsby L, Moore B, Inturrisi BB (December 1966). "A double-blind study of thozalinone (C1 39,808) in depressed outpatients". Current Therapeutic Research, Clinical and Experimental. 8 (12): 621–2. PMID 4962734.
- ↑ "Cylert (Pemoline)" (PDF). FDA. December 2002.
- ↑ https://www.ncbi.nlm.nih.gov/pubmed/11083709
- ↑ Marotta, P. J., & Roberts, E. A. (1998). Pemoline hepatotoxicity in children. The Journal of Pediatrics, 132(5), 894-897.
- ↑ http://www.drugabuse.gov/drugs-abuse/emerging-trends
- ↑ 6.0 6.1 6.2 Shoptaw, S. J., Kao, U., & Ling, W. (2009). Treatment for amphetamine psychosis. The Cochrane Library.
- ↑ Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.
- ↑ 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. eISSN 1937-6995. ISSN 1556-9039. OCLC 163567183.
- ↑ "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG)" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 28, 2019.
- ↑ "Neue-psychoaktive-Stoffe-Gesetz (NpSG)" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 28, 2019.
- ↑ "§ 2 AMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 28, 2019.
- ↑ Prof. Dr. Helmut Pollähne (July 11, 2014). "Cannabinoide Kräutermischungen vor dem EuGH: Legal Highs bleiben legal" [Cannabinoid herbal mixtures at the ECJ: Legal highs stay legal] (in German). LTO. Retrieved December 28, 2019.
- ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
- ↑ https://www.law.cornell.edu/uscode/text/21/813