BOH (drug)

BOH, also known as 3,4-methylenedioxy-β-methoxyphenethylamine or as β-methoxy-MDPEA, is a drug of the phenethylamine, MDxx, and BOx families.^[1] It is the β-methoxy analogue of 3,4-methylenedioxyphenethylamine (MDPEA) and is also more distantly related to methylone (β-keto-MDMA).^[1]

BOH

Clinical data
Other names	β-MeO-MDPEA; β-Methoxy-MDPEA; 3,4-Methylenedioxy-β-methoxyphenethylamine
MedlinePlus	a609035
Routes of administration	Oral[1]
Drug class	Psychoactive drug
ATC code	None
Legal status
Legal status	US: Schedule I (isomer of MDOH) In general: uncontrolled
Pharmacokinetic data
Duration of action	6–8 hours[1]
Identifiers
IUPAC name 2-(1,3-benzodioxol-5-yl)-2-methoxyethanamine
CAS Number	73304-06-0 N
PubChem CID	44719487
ChemSpider	21106264 Y
UNII	W7KI9V2RCE
CompTox Dashboard (EPA)	DTXSID10660351
Chemical and physical data
Formula	C10H13NO3
Molar mass	195.218 g·mol−1
3D model (JSmol)	Interactive image
SMILES NCC(OC)c1ccc2OCOc2c1
InChI InChI=1S/C10H13NO3/c1-12-10(5-11)7-2-3-8-9(4-7)14-6-13-8/h2-4,10H,5-6,11H2,1H3 Y Key:KUTKTMOZFCYDLZ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists BOH's dose range as 80 to 120 mg orally and its duration as 6 to 8 hours.^[1] The effects of BOH were reported to include distinct body awareness, a faint sense of inner warmth, mild mood enhancement, pupil dilation, skin prickling, bodily discomfort, loose bowels, decreased appetite, thirstiness, vague nausea, and cold feet.^[1] There were no clear psychedelic, entactogenic, or euphoriant effects described.^[1]

Pharmacology

Pharmacodynamics

On account of its structural similarity to norepinephrine, BOH might be purely adrenergic in nature.^[1]

Chemistry

Synthesis

The chemical synthesis of BOH has been described.^[1]

Analogues

Analogues of BOH include 3,4-methylenedioxyphenethylamine (MDPEA; homopiperonylamine), 3C-BOH (α-methyl-BOH), BOB (β-methoxy-2C-B), BOD (β-methoxy-2C-D), and methylone (β-keto-MDMA), among others.^[1]

History

BOH was first described in the scientific literature by Alexander Shulgin, Peyton Jacob III, and Darrell Lemaire in 1985.^[2] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]

Society and culture

Legal status

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.^[3]

See also

• Substituted methylenedioxyphenethylamine
• BOx (psychedelics)