5-MAPB (1-(benzofuran-5-yl)-''N''-methylpropan-2-amine) is an
entactogenic
designer drug
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Des ...
similar to
MDMA
3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for Recreational dru ...
in its structure and effects.
Legal Status
Canada
5-MAPB is not listed itself in the CDSA but since it is structurally related to
MDMA
3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for Recreational dru ...
it may be considered illegal in Canada, although this has not been tested in court.
China
As of October 2015 5-MAPB is a controlled substance in China.
Luxembourg
As of July 2021, 5-MAPB is not cited in the list of prohibited substances. Therefore, it is still a legal substance.
United Kingdom
5-MAPB was originally banned in the UK in June 2013 under a
Temporary class drug
A temporary class drug is a relatively new status for controlled drugs, which has been adopted in some jurisdictions, notably New Zealand and the United Kingdom, to attempt to bring newly synthesised designer drugs under legal control. The controll ...
order.
On March 5, 2014, the UK Home Office announced that 5-MAPB would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.
Pharmacokinetics
Metabolism and toxicity
Little formal knowledge exists on 5-MAPB. It does not form the
alpha-methyldopamine
α-Methyldopamine (α-Me-DA), also known as 3,4-dihydroxyamphetamine (3,4-DHA or HHA), is a research chemical of the catecholamine and substituted amphetamine, amphetamine chemical classes. Its bis-glutathione, glutathionyl metabolite is slight ...
metabolite that contributes to the
neurotoxicity
Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specificall ...
of
MDMA
3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for Recreational dru ...
or
MDA
MDA, mda, or ''variation'', may refer to:
Places
* Moldova, a country in Europe with the ISO 3166-1 country code MDA Politics
* Meghalaya Democratic Alliance (2018), ruling coalition government in the Indian State of Meghalaya led by National Pe ...
. A study in rats indicated that the major metabolites of 5-MAPB are
5-APB
5-APB (abbreviation of "5-(2-aminopropyl)benzofuran"; see infobox for the correct IUPAC name) is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes. 5-APB and oth ...
and 3-carboxymethyl-4-hydroxymethamphetamine.
Pharmacodynamics
5-MAPB binds to the dopamine transporter in rat brain cells with a lower affinity than cocaine. ''
In silico
In biology and other experimental sciences, an ''in silico'' experiment is one performed on computer or via computer simulation. The phrase is pseudo-Latin for 'in silicon' (correct la, in silicio), referring to silicon in computer chips. It ...
'' data suggests that the primary action on dopamine is through reversal of the transporter to release dopamine. This is consistent with the effects and it is possible that it exerts a similar action on
serotonin
Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vas ...
and norepinephrine transporters.
References
{{Phenethylamines
Methamphetamines
5-Benzofuranethanamines
Designer drugs
Entactogens and empathogens