Cyclazodone

Summary sheet: Cyclazodone

Cyclazodone
Chemical Nomenclature
Common names	Cyclazodone
Substitutive name	N-Cyclopropylpemoline
Systematic name	2-(Cyclopropylamino)-5-phenyl-1,3-oxazol-4-one
Class Membership
Psychoactive class	Stimulant
Chemical class	Aminorex
Routes of Administration
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section. ⇣ Oral Dosage Threshold 5 mg Light 5 - 15 mg Common 15 - 25 mg Strong 25 - 60 mg Heavy 60 mg + Liver damage may result from heavy or sustained usage. Duration Total 5 - 7 hours Onset 20 - 45 minutes DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
Interactions
Alcohol
MXE
Dissociatives
DXM
MDMA
Stimulants
25x-NBOMe
25x-NBOH
Tramadol

N-Cyclopropylpemoline (also known as Cyclazodone) is a novel stimulant substance of the 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.

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.

It is strongly advised to use harm reduction practices if using this substance.

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).

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. 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.

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. 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.

Pharmacodynamics

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. 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 cognitive and physical stimulation within the user.

Subjective effects

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 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

• • 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.
  • 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.
  • Stamina enhancement
  • Abnormal heartbeat
  • Increased heart rate - Cyclazodone is reported to elevate heart rate to a greater degree than amphetamine.
  • Increased blood pressure
  • Appetite suppression
  • Bronchodilation
  • Dehydration
  • Dry mouth
  • Frequent urination
  • Increased bodily temperature
  • Increased perspiration
  • Nausea - Typically a result of dosing for prolonged periods of time and dehydration.
  • Pain relief
  • Pupil dilation - This effect is typically experienced only at higher dosages and is more prominent on the comedown.
  • Teeth grinding - This component is reported to be less intense compared toMDMA, and only prominent when dosing for prolonged periods of time.
  • Temporary erectile dysfunction
  • Vasoconstriction
  • Restless legs
  • Muscle cramps

Visual effects

• 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.

Cognitive effects

• • 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 - 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.
  • Compulsive redosing
  • Delusion
  • Disinhibition
  • 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.
  • Emotion suppression
  • Focus enhancement
  • Increased libido
  • Increased music appreciation
  • Motivation enhancement
  • Bodily control enhancement
  • Thought acceleration
  • Thought organization
  • Wakefulness
  • 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:
  • Anxiety
  • Cognitive fatigue
  • Delusion
  • Depersonalization
  • Depression
  • Headaches
  • Irritability
  • Motivation suppression
  • Psychosis
  • 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 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; 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.

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.

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 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 all dopaminergic stimulants, meaning that after the consumption of cyclazodone all stimulants will have a reduced effect.

Psychosis

Main article: 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, hallucinations, or delusions). A review on the treatment for amphetamine and methamphetamine abuse-induced psychosis states that about 5–15% of users fail to recover completely. The same review asserts that based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis. 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.

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 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 - 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 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) or the NpSG (New Psychoactive Substances Act). According to §2 AMG (Medicines Act) it would fall under the definition of a medicine because it induces pharmacological effect. By a decision of the European Court of Justice, this definition was declared ineffective because it was not compatible with EU law. Cyclazodone can be considered legal.
• Switzerland: Cyclazodone is not controlled under Buchstabe A, B, C and D. It could be considered legal.
• 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 when intended for human consumption.

See also

• Responsible use
• Research chemicals
• Stimulants
• Releasing agent
• Amphetamine
• 4-Methylaminorex

External links

• Cyclazodone (Wikipedia)
• Cyclazodone (Isomer Design)

Literature

• 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