[(2S)-1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine

ID: ALA195390

Chembl Id: CHEMBL195390

Cas Number: 66142-89-0

PubChem CID: 854031

Max Phase: Preclinical

Molecular Formula: C11H15NO2

Molecular Weight: 193.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (S)-3,4-Methylenedioxymethamphetamine | 66142-89-0|(2S)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine|(S)-(+)-3,4-MDMA (hydrochloride)|(S)-MDMA|(+)-3,4-methylenedioxymethamphetamine|Ecstasy, (S)-|Midomafetamine, (S)-|Mandy, (S)-|Molly, (S)-|Mdma, (S)-|(S)-N-BoC-Isoleucinenitrile|9B6GK297FN|CHEMBL195390|MDMA, R(-)|SCHEMBL15162286|SCHEMBL24088997|BDBM85332|(+)-Methylenedioxymethamphetamine|1,3-Benzodioxole-5-ethanamine, N,alpha-dimethyl-, (alphaS)-|DTXSID101299461|PDSP1_001409|PDSP2_001393|(S)-3Show More⌵

Canonical SMILES:  CN[C@@H](C)Cc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3/t8-/m0/s1

Standard InChI Key:  SHXWCVYOXRDMCX-QMMMGPOBSA-N

Alternative Forms

1. Parent:

   

   ALA195390

   (2S)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 193.25

Molecular Weight (Monoisotopic): 193.1103

AlogP: 1.57

#Rotatable Bonds: 3

Polar Surface Area: 30.49

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.14

CX LogP: 1.86

CX LogD: -0.76

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.79

Np Likeness Score: 0.11

References

1. Nichols DE, Hoffman AJ, Oberlender RA, Jacob P, Shulgin AT..  (1986)  Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.,  29  (10): [PMID:3761319] [10.1021/jm00160a035]

2. Nichols DE, Lloyd DH, Hoffman AJ, Nichols MB, Yim GK..  (1982)  Effects of certain hallucinogenic amphetamine analogues on the release of [3H]serotonin from rat brain synaptosomes.,  25  (5): [PMID:7086839] [10.1021/jm00347a010]

3. Keizers PH, de Graaf C, de Kanter FJ, Oostenbrink C, Feenstra KA, Commandeur JN, Vermeulen NP..  (2005)  Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.,  48  (19): [PMID:16162012] [10.1021/jm050338+]

4. Lewin AH, Miller GM, Gilmour B..  (2011)  Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.,  19  (23): [PMID:22037049] [10.1016/j.bmc.2011.10.007]

5. Llabrés S, García-Ratés S, Cristóbal-Lecina E, Riera A, Borrell JI, Camarasa J, Pubill D, Luque FJ, Escubedo E..  (2014)  Molecular basis of the selective binding of MDMA enantiomers to the alpha4beta2 nicotinic receptor subtype: synthesis, pharmacological evaluation and mechanistic studies.,  81  [PMID:24942641] [10.1016/j.ejmech.2014.04.044]

6. Glennon RA..  (2017)  The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.,  60  (7): [PMID:28244748] [10.1021/acs.jmedchem.7b00085]

Source

Source(1):

• Scientific Literature