N-Methyl-Cyclazodone, ≥98%

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N-Methyl-Cyclazodone is an approximately 4x - 6x more potent derivative of the nootropic and psychostimulant compound Pemoline.

Chemical Name2-(Cyclopropyl(methyl)amino)-5-phenyl-1,3-oxazol-4-one
CAS Number14461-92-8
FormWhite or off-white powder
Molecular Weight230.26 g/mol
Melting Point94-95°C
Molecular FormulaC13H14N2O2
Synonyms  N-Cyclopropyl-N-Methylpemoline, 2-(Cyclopropyl(methyl)amino)-5-phenyl-2-oxazolin-4-one, 2-(Cyclopropyl(methyl)amino)-5-phenyloxazol-4(5H)-one, LD 4202

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Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.

Chemical Information

CAS Number:14461-92-8
Molecular Weight:230.26 g/mol
Melting Point:94-95°C
Molecular Formula:C13H14N2O2
Synonyms:N-Cyclopropyl-N-Methylpemoline, 2-(Cyclopropyl(methyl)amino)-5-phenyl-1,3-oxazol-4-one, 2-(Cyclopropyl(methyl)amino)-5-phenyl-2-oxazolin-4-one, 2-(Cyclopropyl(methyl)amino)-5-phenyloxazol-4(5H)-one, LD 4202
PubChem CID:NA

Technical Information

Application:N-Methyl-Cyclazodone is an approximately 4x - 6x more potent derivative of the nootropic and psychostimulant compound Pemoline.
Appearance:White or off-white powder
Physical State:Solid
Solubility:Soluble to 5 mM in Ethanol, Insoluble in Water.
Storage:Store at room temperature or cooler, in a sealed airtight container, protected from heat, light and humidity.
Stability:Stable for at least two years when stored as above.


WARNING: Unconfirmed online reports claim that consumption of N-Methyl-Cyclazodone may cause fulminant liver failure requiring liver transplant.  This product is not approved for human consumption, and is offered for research purposes only!

Scientific research:

N-Methyl-Cyclazodone (N-Cyclopropyl-N-Methyl-Pemoline) is an approximately 4x - 6x more potent derivative of Pemoline. According to patents filed by the inventors, N-Methyl-Cyclazodone provided particularly strong central stimulant and motor excitant properties, such that a dose of 1 mg/kg in the mouse proved the compound to be equal in potency to d-amphetamine, but longer lasting in effect. The anorexigenic effect of the compound was also similar to that of d-amphetamine; however, unlike d-amphetamine, the compound was not a convulsant, had substantially lower toxicity, and had only a very slight cardiovascular effect in doses up to 5 mg/kg parenterally in the cat or dog.[1][2]

The patents further stated that the new 5-phenyl-2-cyclopropylamino-4-oxazolinone compounds, N-Methyl-Cyclazodone and Cyclazodone, could be employed for therapeutic purposes as follows: "I. As a psychotonic drug in depressive states having various causes, to combat physical and mental asthenia and to increase the psychic tonus and the power of concentration and attention: in states in which anxiety with inhibition constitutes a dominant symptom, to produce the reappearance of "spirit", with the resumption of rational activity and the power to analyze facts logically. II. As an "anti-fatigue" agent, by means of which it is possible to postpone the hour of normal sleep without inhibiting sleep on retiring to bed. III. As an anorexigenic."[1] The patent proceeded to include within the scope of the invention, pharmaceutical compositions comprising N-Methyl-Cyclazodone in a form suitable for oral administration, with a daily dose of 1mg to 50mg, with unit doses containing 1mg to 10mg being generally suitable. [2]

Furthermore, like Thozalinone, N-Methyl-Cyclazodone is an N,N-disubstituted pemoline derivative. As an N,N-disubstituted compound, the literature indicates that Thozalinone shows milder and less potent, but potentially more sustained stimulant and antidepressant effects than N-monoalkyl pemoline derivatives. By analogy, this could suggest the possibility that the pharmacological effects of N-Methyl-Cyclazodone could be longer lasting than those of Cyclazodon

The related parent compound, Pemoline, itself is considered dopaminergic, but its precise method of action hasn't been definitively determined.[3] Pemoline has minimal affinity for norepinephrine receptors, and thus has minimal sympathomimetic side effects compared with typical dopaminergic central nervous system stimulants such as methylphenidate and dexamphetamine.

Interestingly, Pemoline also 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. Furthermore, anecdotal evidence has hinted that pemoline and some related compounds in the 2-amino-5-aryl oxazoline and 2-amino-5-aryl-4-oxazolidinone classes 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 dexamphetamine.

N-Methyl-Cyclazodone is structurally most closely related, not to Pemoline itself, but to Thozalinone (N,N-dimethyl pemoline) - which has been more extensively studied than N-Methyl-Cyclazodone, and which has been described as belonging to a class of "excitants with unique properties distinguishing them from the sympathomimetic amines"[4]. Thozalinone has undergone human clinical trials investigating its potential use in the treatment of depression[5] and obesity[6], and was described as "most interesting", because of its "potency, safety, and duration of action"[4]. In the early 1960s, a detailed comparison was made between the pharmacological effects of thozalinone and amphetamine in several animal species, with the following findings:

  • Thozalinone was approximately one-third as potent as amphetamine by weight when administered orally in mice.
  • Thozalinone was, however, only approximately one-sixth to one-tenth as toxic as amphetamine administered orally.
  • Thozalinone did not cause tremors or convulsions, in contrast to Amphetamine.
  • Thozalinone showed no evidence of tolerance to its effects when administered to rats orally for 11 consecutive days.
  • Thozalinone increased locomotor activity and exploratory behavior in mice with a rapid onset, for longer than 8 hours.
  • Thozalinone was effective from 7.5mg/kg up to 960 mg/kg orally in mice before showing disruptive toxicity.
  • Amphetamine produced similar effects, but with a longer onset time, and a shorter duration than Thozalinone in mice.
  • Amphetamine had a minimum effective dose of 10 mg/kg and a maximum testable level of 160 mg/kg before toxicity.
  • Thozalinone did not affect the temperature of mice when administered from 30 mg/kg up to 120 mg/kg orally.
  • Amphetamine significantly elevated the temperature of mice when administered at 20 mg/kg up to 40 mg/kg orally.
  • Thozalinone (15+ mg/kg orally) and Amphetamine (10+ mg/kg orally) were both able to reduce Reserpine induced sedation.
  • Thozalinone (2+ mg/kg IP) and Amphetamine (1+ mg/kg IP) were both able to prevent Tetrabenazine induced depression.
  • Thozalinone increased locomotor activity and increased exploratory behavior from 2 mg/kg up to 64 mg/kg orally in rats.
  • Amphetamine produced similar effects from 5 mg/kg but was only tested up to 20 mg/kg orally in rats.
  • Thozalinone produced excitation in cats at 10 mg/kg - 20 mg/kg orally. Excitation was marked and lasted for >7 hours.
  • Thozalinone at toxic 500 mg/kg doses did not produce ataxia, hyperesthesia, change in respiration, nor convulsions.
  • Amphetamine caused excitation in cats at 10 mg/kg orally equal to that of 20 mg/kg of Thozalinone orally.
  • Amphetamine at much lower toxic doses caused tachycardia, hypertension, hyperventilation, tremors and convulsions.
  • Thozalinone produced excitement and mydriasis in dogs 10 mg/kg orally which lasted as long as 8 hours.
  • Thozalinone showed no significant changes in arterial blood pressure or heart rate in rats (35mg/kg orally)
  • Thozalinone had no efect on blood pressure or heart rate in dogs (1 mg/kg up to 10 mg/kg intravenously).
  • Amphetamine caused a 40-55 mm rise in blood pressure and tachycardia in dogs (at 1 mg/kg intravenously).
  • Thozalinone caused no side effects or overt changes in behavior when administered intravenously to the dogs.
  • Amphetamine caused hyperactivity, lacrimation and marked exophthalmia when administered intravenously to the dogs.
  • Thozalinone did not exhibit MAO inhibition at a concentration of 0.15 mg/mL (approximately 10^-3 M).
  • Amphetamine showed a 65% MAO inhibition at 10^-3 M.
  • Thozalinone was more effective than Amphetamine at decreasing food consumption over a 6-hour period.

It was concluded on the basis of the above research that Thozalinone had a unique profile, which was partly similar to mood elevating and euphoric stimulants such as the sympathomimetic amines, yet also showed similarity to other classes of antidepressants including deanol, due to having a high therapeutic index and no cardiovascular side effects. Thozalinone was described as causing "increased purposeful behavior" in mice, and causing similar excitement in rats, cats, and dogs as amphetamine, but without increasing blood pressure or leading to other adverse sympathomimetic effects.

The paper reviewing the pharmacological properties of Thozalinone[4] concluded as follows:

"Amphetamine has the relatively low therapeutic index of 9 for grouped mice and 30 for isolated mice. (The "therapeutic index” is defined as the ratio between the LD50 and the least excitant dosage.) The therapeutic index for thozalinone is relatively high, namely, 75 for grouped mice and 270 for individual mice. Death following amphetamine was preceded by tremors and convulsions, but these were never observed with thozalinone... Thozalinone and its structural relatives are believed to be a class of nonconvulsive stimulants.

The pharmacologic actions of a closely related congener (pemoline) have been investigated, and this drug is characterized as a central stimulant with relatively low toxicity and with activity lying between that of amphetamine and caffeine. Psychological testing in man demonstrated that this agent is unique in its mode of action in that the cortical and frontal areas of the brain are affected rather than the brainstem or lower centers. More discrete experimentation on its effect on behavior in... primates and on neurophysiological phenomena, in addition to clinical observation, is necessary to confirm speculation that thozalinone exerts its effects in a manner different from that of other known excitants.

SUMMARY: Thozalinone has been shown to possess some pharmacologic actions similar to those of amphetamine and imipramine, but with important differences. It is less toxic than amphetamine, and its margin of safety in mice is greater. The stimulant action does not progress to tremors or convulsions as the dosage is increased. The anorexigenic activity of thozalinone is more pronounced and longer lasting than that of amphetamine. There is no evidence of the development of tolerance. The cardiovascular side effects of thozalinone are minimal and analeptic actions are absent."


  • [1] Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolinone. Les Laboratoires Dausse, assignee. Patent US3609159. 28 Sept. 1971.
  • [2] Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. New Oxazolinones. Les Laboratoires Dausse, assignee. Patent GB1109470. 22 Sept. 1966.
  • [3] "Cylert (Pemoline)" (PDF). FDA. December 2002.
  • [4] Greenblatt EN, Osterberg AC. Some pharmacologic properties of thozalinone, a new excitant. Toxicol Appl Pharmacol. 1965;7(4):566-78.
  • [5] Gallant DM, Bishop MP, Scrignar CB, Hornsby L, Moore B, Inturrisi BB. A double-blind study of thozalinone (C1 39,808) in depressed outpatients. Curr Ther Res Clin Exp. 1966;8(12):621-2.
  • [6] Leite AC, Liepen LL, Costa VP. [Clinical trial of Stimsem Thozalinone in the treatment of obese patients]. Rev Bras Med. 1971;28(9):475-8.

Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.

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