3-MMC: Difference between revisions

Line 14:

==Chemistry==

3-MMC, or 3-Methylmethcathinone, is a ~~molecule~~ of ~~the substituted cathinone class~~. Cathinones are a sub-category of [[amphetamines]], ~~sharing~~ the core amphetamine structure of a phenyl ring bound to an amino (NH2) group through an ethyl chain and an additional methyl substitution at Rα.

3-MMC, or 3-Methylmethcathinone, belongs to a class of synthetic organic compounds known as cathinones. Cathinones are a sub-category of [[amphetamines]], meaning they share the core amphetamine structure of a phenyl ring bound to an amino (NH2) group through an ethyl chain, and an additional methyl substitution at Rα.

~~3-MMC and other cathinones~~ are differentiated by their ketone substitution on the beta carbon of the amphetamine skeleton, meaning they are β-keto-amphetamines. 3-MMC has two methyl substitutions on its cathinone skeleton, one at R3 of the phenyl ring, and a second at the nitrogen group RN. ~~3-MMC is analogous to [[mephedrone]]; it is identical in structure except for the placement of the methyl group at R4 instead of R3~~

Cathinones are differentiated by their ketone substitution on the beta carbon of the amphetamine skeleton, meaning they are β-keto-amphetamines. 3-MMC has two methyl substitutions on its cathinone skeleton, one at R3 of the phenyl ring, and a second at the nitrogen group RN.

~~3-MMC contains~~ a ~~chiral centre at the C-2 carbon~~ of ~~the propane side-chain~~, ~~so that two enantiomers exist: R-3-MMC and S-3-MMC. Due to~~ the ~~similarity with cathinone the S form is thought to be more potent than~~ the R ~~form.~~<~~ref name="who"~~>~~https:~~/~~/www.who.int/medicines/access/controlled-substances/4.4_3-MMC_CritReview.pdf~~</~~ref~~>

It is considered a structural analog of [[mephedrone]], meaning it is identical in structure except for the placement of the methyl group at R4 instead of R3

The hydrochloride salt of 3-MMC is a white crystalline powder. It has a melting point of 193.2 ± 0.2°C (hydrochloride salt) and a boiling point of 280.5 ± 23.0°C at 760 mm Hg. It is sparingly soluble in PBS; slightly soluble in ethanol, dimethyl sulfoxide, and dimethyl formamide.<ref name="who" />

It is a chiral compound with a stereocenter at R2 of the propane side-chain. Two enantiomers exist: R-3-MMC and S-3-MMC. Due to the similarity with cathinone proper, the S form is thought to be more potent than the R form.<ref name="who">https://www.who.int/medicines/access/controlled-substances/4.4_3-MMC_CritReview.pdf</ref>

The hydrochloride salt of 3-MMC occurs as a white crystalline powder. It has a melting point of 193.2 ± 0.2°C (hydrochloride salt) and a boiling point of 280.5 ± 23.0°C at 760 mm Hg. It is sparingly soluble in PBS; slightly soluble in ethanol, dimethyl sulfoxide, and dimethyl formamide.<ref name="who" />

==Pharmacology==

@@ Line 14: / Line 14: @@
 ==Chemistry==
--MMC, or 3-Methylmethcathinone, is a molecule of the substituted cathinone class. Cathinones are a sub-category of [[amphetamines]], sharing the core amphetamine structure of a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and an additional methyl substitution at R<sub>α</sub>.
+-MMC, or 3-Methylmethcathinone, belongs to a class of synthetic organic compounds known as cathinones. Cathinones are a sub-category of [[amphetamines]], meaning they share the core amphetamine structure of a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain, and an additional methyl substitution at R<sub>α</sub>.
--MMC and other cathinones are differentiated by their ketone substitution on the beta carbon of the amphetamine skeleton, meaning they are β-keto-amphetamines. 3-MMC has two methyl substitutions on its cathinone skeleton, one at R<sub>3</sub> of the phenyl ring, and a second at the nitrogen group R<sub>N</sub>. 3-MMC is analogous to [[mephedrone]]; it is identical in structure except for the placement of the methyl group at R<sub>4</sub> instead of R<sub>3</sub>
+Cathinones are differentiated by their ketone substitution on the beta carbon of the amphetamine skeleton, meaning they are β-keto-amphetamines. 3-MMC has two methyl substitutions on its cathinone skeleton, one at R<sub>3</sub> of the phenyl ring, and a second at the nitrogen group R<sub>N</sub>.
--MMC contains a chiral centre at the C-2 carbon of the propane side-chain, so that two enantiomers exist: R-3-MMC and S-3-MMC. Due to the similarity with cathinone the S form is thought to be more potent than the R form.<ref name="who">https://www.who.int/medicines/access/controlled-substances/4.4_3-MMC_CritReview.pdf</ref>
+It is considered a structural analog of [[mephedrone]], meaning it is identical in structure except for the placement of the methyl group at R<sub>4</sub> instead of R<sub>3</sub>
-The hydrochloride salt of 3-MMC is a white crystalline powder. It has a melting point of 193.2 ± 0.2°C (hydrochloride salt) and a boiling point of 280.5 ± 23.0°C at 760 mm Hg. It is sparingly soluble in PBS; slightly soluble in ethanol, dimethyl sulfoxide, and dimethyl formamide.<ref name="who" />
+It is a chiral compound with a stereocenter at R<sub>2</sub> of the propane side-chain. Two enantiomers exist: R-3-MMC and S-3-MMC. Due to the similarity with cathinone proper, the S form is thought to be more potent than the R form.<ref name="who">https://www.who.int/medicines/access/controlled-substances/4.4_3-MMC_CritReview.pdf</ref>
+The hydrochloride salt of 3-MMC occurs as a white crystalline powder. It has a melting point of 193.2 ± 0.2°C (hydrochloride salt) and a boiling point of 280.5 ± 23.0°C at 760 mm Hg. It is sparingly soluble in PBS; slightly soluble in ethanol, dimethyl sulfoxide, and dimethyl formamide.<ref name="who" />
 ==Pharmacology==