G-130 (GP-130, 2-Phenyl-5,5-dimethyltetrahydro-1,4-oxazine)
is a drug with
stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
and
anorectic
An anorectic or anorexic is a drug which reduces appetite, resulting in lower food consumption, leading to weight loss. By contrast, an appetite stimulant is referred to as orexigenic.
The term is (from the Greek ''ἀν-'' (an-) = "without" a ...
effects, related to
phenmetrazine
Phenmetrazine ( INN, USAN, BAN) (brand name Preludin, and many others) is a stimulant drug first synthesized in 1952 and originally used as an appetite suppressant, but withdrawn from the market in the 1980s due to widespread abuse. It was initi ...
.
Structural analogs
Compounds related to G-130 and
radafaxine
Radafaxine (developmental code name GW-353,162), also known as (2''S'',3''S'')-hydroxybupropion or (''S'',''S'')-hydroxybupropion, is a norepinephrine–dopamine reuptake inhibitor (NDRI) which was under development by GlaxoSmithKline in the 20 ...
were synthesized that behave as combined
inhibitors of monoamine uptake and
nicotinic acetylcholine receptor
Nicotinic acetylcholine receptors, or nAChRs, are receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the central and peripheral ne ...
s.
Synthesis
![G-130 synthesis](https://upload.wikimedia.org/wikipedia/commons/0/02/G-130_synthesis.svg)
Ex 1: 2 moles of 2-methyl-2-aminopropanol (
aminomethyl propanol
Aminomethyl propanol is an organic compound with the formula H2NC(CH3)2CH2OH. It is colorless liquid that is classified as an alkanolamine. It is a useful buffer and a precursor to numerous other organic compounds.
Synthesis
Aminomethyl propano ...
) (1) is reacted with 1 moles of
styrene oxide (phenyloxirane)
6-09-3(2) in 0.2 mole water.
Ex 2:
Fepradinol 6981-91-6 3075-47-8(3) is treated with acid, to cyclize to the morpholine ring.
See also
*
2-Phenyl-3,6-dimethylmorpholine
2-Phenyl-3,6-dimethylmorpholine is a drug with stimulant and anorectic effects, related to phenmetrazine. Based on what is known from other phenylmorpholines with similar structure, it likely acts as a serotonin reuptake inhibitor and may produc ...
*
3-Fluorophenmetrazine
*
4-Methylphenmetrazine
*
Phendimetrazine
Phendimetrazine (Bontril, Adipost, Anorex-SR, Appecon, Melfiat, Obezine, Phendiet, Plegine, Prelu-2, Statobex) is a stimulant drug of the morpholine chemical class used as an appetite suppressant.
Pharmacology
Phendimetrazine functions as a p ...
*
Manifaxine
Manifaxine (developmental code name GW-320,659) is a norepinephrine–dopamine reuptake inhibitor developed by GlaxoSmithKline through structural modification of radafaxine, an isomer of hydroxybupropion and one of the active metabolites of bup ...
References
Stimulants
Phenylmorpholines
Designer drugs
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