BOx, also known as β-hydroxy- or -methoxy- and ring-substituted phenethylamines, are a group of

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

and other

psychoactive drug A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

s of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

family. They have either a

hydroxy group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

methoxy group In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

at the β position of the

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...

side chain In organic chemistry and biochemistry, a side chain is a substituent, chemical group that is attached to a core part of the molecule called the "main chain" or backbone chain, backbone. The side chain is a hydrocarbon branching element of a mo ...

as well as additional

substitution Substitution may refer to: Arts and media *Substitution (poetry), a variation in poetic scansion * Substitution (theatre), an acting methodology Music *Chord substitution, swapping one chord for a related one within a chord progression *Tritone ...

s at the 2 through 5 positions of the

phenyl ring In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

. The BOx drugs were synthesized and tested by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

and reported in his 1991 book ''

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

'' (''Phenethylamines I Have Known and Loved'').

List of BOx drugs

The BOx drugs include the following, with their effects as reported by Shulgin also specified: * BOB (4-bromo-2,5,β-trimethoxyphenethylamine) – methoxy BOx analogue of

2C-B 2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine or by the slang name Nexus, is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. It was first synthesized by Alexander Shulgin in 1974 for use in psychoth ...

– altered state of consciousness, tinnitus, tingling, sense of awareness * BOH-2C-B (β-OH-2C-B) – hydroxy BOx analogue of

– encountered as a novel

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. ...

and presumably a psychedelic * BOD (4-methyl-2,5,β-trimethoxyphenethylamine) – methoxy BOx analogue of

2C-D 2C-D, also known as 2C-M or as 2,5-dimethoxy-4-methylphenethylamine, is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, a ...

– mild open-eye and moderate closed-eye visuals, enhanced conversation and humor, nausea and lethargy *

BOHD BOHD (4-methyl-2,5-dimethoxy-beta-hydroxyphenethylamine) is a lesser-known drug of the BOx group. It is the beta- hydroxy derivative of 2C-D. BOHD was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', the minimum dosage is listed as ...

(4-methyl-2,5-dimethoxy-β-hydroxyphenethylamine) – hydroxy BOx analogue of

– marked drop in blood pressure * BOH (3,4-methylenedioxy-β-methoxyphenethylamine) – methoxy BOx analogue of MDPEA –slight warmth, mydriasis, anorexia, mild nausea, cold feet, no psychedelic, entactogenic, or euphoriant effects (however nonetheless given a ++ on the Shulgin scale) * BOM (3,4,5,β-tetramethoxyphenethylamine) – methoxy BOx analogue of

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

– few or no effects * DME (3,4-dimethoxy-β-hydroxyphenethylamine) – hydroxy BOx analogue of

3,4-dimethoxyamphetamine 3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. The drug has been assessed ...

(3,4-DMA) – few or no effects Hence, of the BOx drugs, BOD is the only one that produces clear psychedelic effects.

References

{{Chemical classes of psychoactive drugs Alexander Shulgin BOx (psychedelics) Chemical classes of psychoactive drugs Psychedelic phenethylamines

List of BOx drugs

See also

References