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Cyclazodone, ≥98%

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Cyclazodone is an approximately 3x - 5x more potent N-cyclopropyl derivative of the nootropic and psychostimulant compound Pemoline.

Chemical Name2-(cyclopropylamino)-5-phenyl-1,3-oxazol-4-one
CAS Number14461-91-7
FormWhite or off-white powder
Molecular Weight216.09 g/mol
Melting Point139-140°C
Molecular FormulaC12H12N2O2
Synonyms N-Cyclopropylpemoline, Cyclopropyl Pemoline, 2-(Cyclopropylamino)-5-phenyl-2-oxazolin-4-one

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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:14461-91-7
Molecular Weight:216.09 g/mol
Melting Point:139-140°C
Molecular Formula:C12H12N2O2
Synonyms: N-Cyclopropylpemoline, Cyclopropyl Pemoline, 2-(cyclopropylamino)-5-phenyl-1,3-oxazol-4-one, 2-(Cyclopropylamino)-5-phenyl-2-oxazolin-4-one
PubChem CID:26701


Technical Information:

Application:Cyclazodone is an approximately 3x - 5x more potent N-cyclopropyl 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.


Scientific research:

Cyclazodone (N-Cyclopropylpemoline) is an approximately 3x - 5x more potent N-cyclopropyl derivative of Pemoline. 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 same time Cyclazodone also offered a much more favorable therapeutic index and margin of safety than Pemoline and other N-lower-alkyl-substituted Pemoline derivatives.[1]

The patents stated that in animal models, Cyclazodone exhibited central nervous system stimulant and antidepressant efficacy and potency at least equal to that of d-amphetamine. The maximum intensity of motive excitation produced by Cyclazodone reached ++++, on a scale of + to ++++, wherein ++++ indicated the greatest motive activity. The duration of maximum activity spanned 180 minutes, and the total duration of excitation was in excess of 6 hours.[1]

Furthermore, according to the inventor's patents, Cyclazodone also possessed anorexic efficacy and potency at least equal to that of d-amphetamine in animal models, yet the toxicity of Cyclazodone was found to be low in comparison with the activity thereof.[2]

The patents concluded that Cyclazodone could be employed as a psychotonic, an "anti-fatigue" agent, and as an anorexigenic, and that Cyclazodone could be produced in a convenient therapeutic form such as tablets containing from 1 to 30 mg of active substance, with a particularly advantageous form for oral administration being a gelatin capsule containing 5mg of Cyclazodone deposited onto an ion-exchange resin.[2]

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.

In particular, 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) - which have been more extensively studied than Cyclazodone, and which have been described as "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. 5-Phenyl-2-Cyclopropylamino-4-Oxazolinone. Les Laboratoires Dausse, assignee. Patent GB1005738A. 29 Sept. 1965.
  • [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.

[Cyclazodone Q4 2018] Cyclazodone.20180902.pdf

[Cyclazodone Q3 2018] Cyclazodone.20180803.pdf

[Cyclazodone Q1 2018] Cyclazodone.20180108.pdf

[Cyclazodone Q3 2017] Cyclazodone.20170724.pdf