2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine

ID: ALA1927025

Chembl Id: CHEMBL1927025

Cas Number: 61614-60-6

PubChem CID: 3046161

Max Phase: Preclinical

Molecular Formula: C10H13NO2

Molecular Weight: 179.22

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: (R)-3,4-Methylenedioxyamphetamine | Tenamfetamine, (-)-|61614-60-6|M3P34V176U|(R)-3,4-Methylenedioxyamphetamine|(R)-Mda|(R)-alpha-Methyl-1,3-benzodioxole-5-ethanamine|MDA,R(-)|(R)-beta-3,4-(Methylenedioxy)amphetamine|UNII-M3P34V176U|(R)-tenamfetamine|(R)-alpha-Methyl-3,4-(methylenedioxy)phenethylamine|1,3-Benzodioxole-5-ethanamine, alpha-methyl-, (R)-|TENAMFETAMINE, (R)-|SCHEMBL9361151|CHEMBL1927025|BDBM86239|MDA, (R)-|Phenethylamine, alpha-methyl-3,4-(methylenedioxy)-, (R)-|MDA (PSYCHEDELIC), (Show More

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

Standard InChI:  InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3/t7-/m1/s1

Standard InChI Key:  NGBBVGZWCFBOGO-SSDOTTSWSA-N

Alternative Forms

Associated Targets(Human)

TAAR1 Tclin Trace amine-associated receptor 1 (1397 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Htr1b Serotonin 1 (5-HT1) receptor (408 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2b Serotonin 2 (5-HT2) receptor (2078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TAAR1 Trace amine-associated receptor 1 (20 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2a Serotonin 2a (5-HT2a) receptor (3540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc6a4 Serotonin transporter (6087 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc6a3 Dopamine transporter (6071 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 179.22Molecular Weight (Monoisotopic): 179.0946AlogP: 1.30#Rotatable Bonds: 2
Polar Surface Area: 44.48Molecular Species: BASEHBA: 3HBD: 1
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 10.01CX LogP: 1.43CX LogD: -1.05
Aromatic Rings: 1Heavy Atoms: 13QED Weighted: 0.74Np Likeness Score: 0.28

References

1. Glennon RA..  (1987)  Central serotonin receptors as targets for drug research.,  30  (1): [PMID:3543362] [10.1021/jm00384a001]
2. 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]
3. 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]
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. 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