(+)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine

ID: ALA468880

Chembl Id: CHEMBL468880

Cas Number: 43061-16-1

PubChem CID: 23983765

Max Phase: Preclinical

Molecular Formula: C11H16BrNO2

Molecular Weight: 274.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C[C@H](C)N)c(OC)cc1Br

Standard InChI:  InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3/t7-/m0/s1

Standard InChI Key:  FXMWUTGUCAKGQL-ZETCQYMHSA-N

Alternative Forms

1. Parent:

   

   ALA468880

   Brolamfetamine, (S)-

2. Alternative Forms:

   

   ALA468880

   S-(+)-2,5-Dimethoxy-4-bromoamphetamine hydrochloride

Molecule Features

Natural Product: No

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: 274.16

Molecular Weight (Monoisotopic): 273.0364

AlogP: 2.36

#Rotatable Bonds: 4

Polar Surface Area: 44.48

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.90

CX LogP: 2.26

CX LogD: -0.14

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.92

Np Likeness Score: 0.09

References

1. Glennon RA, Young R, Benington F, Morin RD..  (1982)  Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.,  25  (10): [PMID:7143352] [10.1021/jm00352a013]

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

3. Glennon RA, Raghupathi R, Bartyzel P, Teitler M, Leonhardt S..  (1992)  Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.,  35  (4): [PMID:1542100] [10.1021/jm00082a014]

4. Glennon RA, Titeler M, Seggel MR, Lyon RA..  (1987)  N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.,  30  (5): [PMID:3572981] [10.1021/jm00388a032]

5. Runyon SP, Mosier PD, Roth BL, Glennon RA, Westkaemper RB..  (2008)  Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation.,  51  (21): [PMID:18847250] [10.1021/jm800771x]

6. 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]

Source

Source(1):

• Scientific Literature