MBDB

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1,3-Benzodioxolyl-N-methylbutanamine

Chemical structure
Clinical data
Other names	Methylbenzodioxolylbutanamine; N-Methyl-1,3-benzodioxolylbutanamine; MBDB; 3,4-Methylenedioxy-N-methyl-butanphenamine; MDMB
Drug class	Empathogen–entactogen; Stimulant
Legal status
Legal status	AU: S9 (Prohibited substance) DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I (Positional Isomer of MDEA)
Pharmacokinetic data
Duration of action	4–6 hours
Identifiers
IUPAC name 1-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amine
CAS Number	135795-90-3 Y
PubChem CID	124844
ChemSpider	111153
UNII	E8HMQ4F9JQ
KEGG	C22786
CompTox Dashboard (EPA)	DTXSID70894039
Chemical and physical data
Formula	C12H17NO2
Molar mass	207.273 g·mol−1
3D model (JSmol)	Interactive image
Melting point	156 °C (313 °F)
SMILES CCC(CC1=CC2=C(C=C1)OCO2)NC
InChI InChI=1S/C12H17NO2/c1-3-10(13-2)6-9-4-5-11-12(7-9)15-8-14-11/h4-5,7,10,13H,3,6,8H2,1-2H3 Key:USWVWJSAJAEEHQ-UHFFFAOYSA-N
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1,3-Benzodioxolyl-N-methylbutanamine (N-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine) is an entactogen of the phenethylamine chemical class. It is known by the street names “Eden” and “Methyl-J.”^[1] MBDB is a ring substituted amphetamine and an analogue of MDMA. Like MDMA, it has a methylene dioxy substitution at the 3 and 4 position on the aromatic ring; this is perhaps the most distinctive feature that structurally define analogues of MDMA, in addition to their unique effects, and as a class they are often referred to as "entactogens" to differentiate between typical stimulant amphetamines that (as a general rule) are not ring substituted. MBDB differs from MDMA by having an ethyl group instead of a methyl group attached to the alpha carbon; all other parts are identical. Modification at the alpha carbon is uncommon for substituted amphetamines. It has IC₅₀ values of 784 nM against 5-HT, 7825 nM against dopamine, and 1233 nM against norepinephrine.^{[citation needed]} Its metabolism has been described in scientific literature.^[2]

MBDB was first synthesized by pharmacologist and medicinal chemist David E. Nichols^{[citation needed]} and later tested by Alexander Shulgin and described in his book, PiHKAL: A Chemical Love Story. MBDB's dosage, according to PiHKAL, is 180–210 mg; the proper dosage relative to body mass seems unknown. Its duration is 4–6 hours, with noticeable after-effects lasting for 1–3 hours.^{[citation needed]}

MBDB was initially developed as a non-psychedelic entactogen. It has lower effects on the dopamine system in comparison to other entactogens such as MDMA.^{[citation needed]} MBDB causes many mild, MDMA-like effects, in particular the lowering of social barriers and inhibitions, pronounced sense of empathy and compassion, and mild euphoria, all of which are present.^{[citation needed]} MBDB tends to produce less euphoria, psychedelia, and stimulation in comparison to MDMA.^{[citation needed]}