Gabapentin: Difference between revisions

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==Chemistry==

Gabapentin, or 1-(aminomethyl)~~cyclohexanacetic~~ acid, is an analogue of the neurotransmitter [[GABA]]. It contains a cyclohexane ring bound to a methylamino chain CH3NH2. At the same location, R1, the cyclohexane ring is also substituted with an acetic acid group. Gabapentin is structurally analogous to GABA. GABA contains an amino group bound to the terminal carbon of a butanoic acid chain. The structure of gabapentin contains the secondary carbon R3 of the butanoic acid chain in GABA incorporated into an attached cyclohexane ring, converting it into a tertiary carbon while still maintaining the chain.

Gabapentin is a 3,3-disubstituted derivative of GABA. Therefore, it is a GABA analogue, as well as a γ-amino acid.<ref>Wyllie E, Cascino GD, Gidal BE, Goodkin HP (17 February 2012). ''Wyllie's Treatment of Epilepsy: Principles and Practice''. Lippincott Williams & Wilkins. p. 423. ISBN <bdi>978-1-4511-5348-4</bdi>.</ref> Specifically, it is a derivative of GABA with a pentyl disubstitution at 3 position, hence, the name - gaba''pentin'', in such a way as to form a six-membered ring. After formation of the ring, the amine and carboxylic groups are not in the same relative positions as they are in the GABA:.<ref>Sneader, Walter (2005). ''Drug Discovery: A History''. John Wiley & Sons. pp. 219–220. ISBN <bdi>978-0-470-01552-0</bdi>.</ref> they are more conformationally constrained.<ref>Levandovskiy IA, Sharapa DI, Shamota TV, Rodionov VN, Shubina TE (February 2011). "Conformationally restricted GABA analogs: from rigid carbocycles to cage hydrocarbons". ''Future Medicinal Chemistry''. '''3''' (2): 223–41. doi:10.4155/fmc.10.287. <nowiki>PMID 21428817</nowiki>.</ref>

Gabapentin, or 1-(aminomethyl)cyclohexylacetic acid, is an analogue of the neurotransmitter [[GABA]]. It contains a cyclohexane ring bound to a methylamino chain CH3NH2. At the same location, R1, the cyclohexane ring is also substituted with an acetic acid group. Gabapentin is structurally analogous to GABA. GABA contains an amino group bound to the terminal carbon of a butanoic acid chain. The structure of gabapentin contains the secondary carbon R3 of the butanoic acid chain in GABA incorporated into an attached cyclohexane ring, converting it into a tertiary carbon while still maintaining the chain.

==Pharmacology==

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 ==Chemistry==
-Gabapentin, or 1-(aminomethyl)cyclohexanacetic acid, is an analogue of the neurotransmitter [[GABA]]. It contains a cyclohexane ring bound to a methylamino chain CH<sub>3</sub>NH<sub>2</sub>. At the same location, R<sub>1</sub>, the cyclohexane ring is also substituted with an acetic acid group. Gabapentin is structurally analogous to GABA. GABA contains an amino group bound to the terminal carbon of a butanoic acid chain. The structure of gabapentin contains the secondary carbon R<sub>3</sub> of the butanoic acid chain in GABA incorporated into an attached cyclohexane ring, converting it into a tertiary carbon while still maintaining the chain.
+Gabapentin is a 3,3-disubstituted derivative of GABA. Therefore, it is a GABA analogue, as well as a γ-amino acid.<ref>Wyllie E, Cascino GD, Gidal BE, Goodkin HP (17 February 2012). ''Wyllie's Treatment of Epilepsy: Principles and Practice''. Lippincott Williams & Wilkins. p. 423. ISBN <bdi>978-1-4511-5348-4</bdi>.</ref> Specifically, it is a derivative of GABA with a pentyl disubstitution at 3 position, hence, the name - gaba''pentin'', in such a way as to form a six-membered ring. After formation of the ring, the amine and carboxylic groups are not in the same relative positions as they are in the GABA:.<ref>Sneader, Walter (2005). ''Drug Discovery: A History''. John Wiley & Sons. pp. 219–220. ISBN <bdi>978-0-470-01552-0</bdi>.</ref> they are more conformationally constrained.<ref>Levandovskiy IA, Sharapa DI, Shamota TV, Rodionov VN, Shubina TE (February 2011). "Conformationally restricted GABA analogs: from rigid carbocycles to cage hydrocarbons". ''Future Medicinal Chemistry''. '''3''' (2): 223–41. doi:10.4155/fmc.10.287. <nowiki>PMID 21428817</nowiki>.</ref>
+Gabapentin, or 1-(aminomethyl)cyclohexylacetic acid, is an analogue of the neurotransmitter [[GABA]]. It contains a cyclohexane ring bound to a methylamino chain CH<sub>3</sub>NH<sub>2</sub>. At the same location, R<sub>1</sub>, the cyclohexane ring is also substituted with an acetic acid group. Gabapentin is structurally analogous to GABA. GABA contains an amino group bound to the terminal carbon of a butanoic acid chain. The structure of gabapentin contains the secondary carbon R<sub>3</sub> of the butanoic acid chain in GABA incorporated into an attached cyclohexane ring, converting it into a tertiary carbon while still maintaining the chain.
 ==Pharmacology==