Talk:N-Methyl-Cyclazodone: Difference between revisions

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'''N-Cyclopropyl-N-Methylpemoline''' (also known as '''N-Methyl-Cyclazodone''' or '''NMC''') is a novel [[psychoactive class::stimulant]] substance of the [[chemical class::4-oxazolidinone]] class. It 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. It should be noted that one of its parent componds, [[thozalinone]], has been used as an [[antidepressant]] in europe<ref>{{cite journal | vauthors = Gallant DM, Bishop MP, Scrignar CB, Hornsby L, Moore B, Inturrisi BB | title = A double-blind study of thozalinone (C1 39,808) in depressed outpatients | journal = Current Therapeutic Research, Clinical and Experimental | volume = 8 | issue = 12 | pages = 621–2 | date = December 1966 | pmid = 4962734 }}</ref>, which may be due to its serotion-releasing properties.

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.

~~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]]~~.

One of its parent compounds, [[thozalinone]], has been used as an [[antidepressant]] in europe<ref>{{cite journal | vauthors = Gallant DM, Bishop MP, Scrignar CB, Hornsby L, Moore B, Inturrisi BB | title = A double-blind study of thozalinone (C1 39,808) in depressed outpatients | journal = Current Therapeutic Research, Clinical and Experimental | volume = 8 | issue = 12 | pages = 621–2 | date = December 1966 | pmid = 4962734 }}</ref>, which may be due to its serotonin-releasing properties.

~~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.

[[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]].

'''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 [[responsible drug 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]].

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]].

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).

N-Methyl-Cyclazodone is structurally most closely related to [[cyclazodone]] 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 [[dopamine|dopaminergic]], but its precise method of action has not been fully determined.<ref>"Cylert (Pemoline)" (PDF). FDA. December 2002.</ref> 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 [[Isomer|dextro]]-amphetamine.

N-Methyl-Cyclazodone is an approximately 4x - 6x more potent N,N-methylcyclopropyl derivative of [[pemoline]]. Pemoline is considered to be [[dopamine|dopaminergic]], but its precise method of action has not been fully determined.<ref>"Cylert (Pemoline)" (PDF). FDA. December 2002.</ref> 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 [[Isomer|dextro]]-amphetamine.

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 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>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent US3609159. 28 Sept. 1971.</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>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent US3609159. 28 Sept. 1971.</ref> 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>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent GB1005738A. 29 Sept. 1965.</ref>

===Pharmacodynamics===

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 '''N-Cyclopropyl-N-Methylpemoline''' (also known as '''N-Methyl-Cyclazodone''' or '''NMC''') is a novel [[psychoactive class::stimulant]] substance of the [[chemical class::4-oxazolidinone]] class. It 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. It should be noted that one of its parent componds, [[thozalinone]], has been used as an [[antidepressant]] in europe<ref>{{cite journal | vauthors = Gallant DM, Bishop MP, Scrignar CB, Hornsby L, Moore B, Inturrisi BB | title = A double-blind study of thozalinone (C1 39,808) in depressed outpatients | journal = Current Therapeutic Research, Clinical and Experimental | volume = 8 | issue = 12 | pages = 621–2 | date = December 1966 | pmid = 4962734 }}</ref>, which may be due to its serotion-releasing properties.
+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.
-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]].
+One of its parent compounds, [[thozalinone]], has been used as an [[antidepressant]] in europe<ref>{{cite journal | vauthors = Gallant DM, Bishop MP, Scrignar CB, Hornsby L, Moore B, Inturrisi BB | title = A double-blind study of thozalinone (C1 39,808) in depressed outpatients | journal = Current Therapeutic Research, Clinical and Experimental | volume = 8 | issue = 12 | pages = 621–2 | date = December 1966 | pmid = 4962734 }}</ref>, which may be due to its serotonin-releasing properties.
-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.
+[[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]].
+'''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 [[responsible drug 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]].
+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]].
-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).
+N-Methyl-Cyclazodone is structurally most closely related to [[cyclazodone]] 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 [[dopamine|dopaminergic]], but its precise method of action has not been fully determined.<ref>"Cylert (Pemoline)" (PDF). FDA. December 2002.</ref> 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 [[Isomer|dextro]]-amphetamine.
+N-Methyl-Cyclazodone is an approximately 4x - 6x more potent N,N-methylcyclopropyl derivative of [[pemoline]]. Pemoline is considered to be [[dopamine|dopaminergic]], but its precise method of action has not been fully determined.<ref>"Cylert (Pemoline)" (PDF). FDA. December 2002.</ref> 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 [[Isomer|dextro]]-amphetamine.
-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 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>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent US3609159. 28 Sept. 1971.</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>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent US3609159. 28 Sept. 1971.</ref> 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>Val De Marne, Don Pierre R. L. Guidicelli, and Henry Najer. 5-Phenyl-2-Cyclopropylamino-4-Oxazolidinone. Les Laboratoires Dausse, assignee. Patent GB1005738A. 29 Sept. 1965.</ref>
 ===Pharmacodynamics===