ID: ALA8642

Max Phase: Preclinical

Molecular Formula: C11H17NO2

Molecular Weight: 195.26

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(OC)c(CC(C)N)c1

Standard InChI:  InChI=1S/C11H17NO2/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3

Standard InChI Key:  LATVFYDIBMDBSY-UHFFFAOYSA-N

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

Properties

Molecular Weight: 195.26

Molecular Weight (Monoisotopic): 195.1259

AlogP: 1.59

#Rotatable Bonds: 4

Polar Surface Area: 44.48

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.91

CX LogP: 1.49

CX LogD: -0.91

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.79

Np Likeness Score: -0.05

References

1. Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA..  (1990)  A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors.,  33  (3): [PMID:2308135] [10.1021/jm00165a023]

2. 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]

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

4. Glennon RA, Schubert E, Jacyno JM, Rosecrans JA..  (1980)  Studies on several 7-substituted N,N-dimethyltryptamines.,  23  (11): [PMID:6779006] [10.1021/jm00185a014]

5. Domelsmith LN, Eaton TA, Houk KN, Anderson GM, Glennon RA, Shulgin AT, Castagnoli N, Kollman PA..  (1981)  Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.,  24  (12): [PMID:7310818] [10.1021/jm00144a009]

6. Glennon RA, McKenney JD, Lyon RA, Titeler M..  (1986)  5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogues.,  29  (2): [PMID:3950904] [10.1021/jm00152a005]

7. Peddi S, Roth BL, Glennon RA, Westkaemper RB..  (2003)  Ring substituted analogues of 5-aminomethyl-10,11-dihydro-dibenzo[a,d]cycloheptene (AMDH): potential modes of binding to the 5-HT(2A) receptor.,  13  (15): [PMID:12852967] [10.1016/s0960-894x(03)00504-3]

8. Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM..  (1991)  2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.,  34  (1): [PMID:1992127] [10.1021/jm00105a043]

9. Glennon RA, Liebowitz SM, Anderson GM..  (1980)  Serotonin receptor affinities of psychoactive phenalkylamine analogues.,  23  (3): [PMID:7365744] [10.1021/jm00177a017]

10. Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA..  (2000)  1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists.,  43  (16): [PMID:10956215] [10.1021/jm9906062]

11. Clare BW..  (1998)  The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens.,  41  (20): [PMID:9748359] [10.1021/jm980144c]

12. Clare BW..  (1990)  Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.,  33  (2): [PMID:2299636] [10.1021/jm00164a036]

13. 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]

14. Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE..  (2005)  Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling.,  48  (7): [PMID:15801832] [10.1021/jm0493109]

15. Parker MA, Kurrasch DM, Nichols DE..  (2008)  The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.,  16  (8): [PMID:18296055] [10.1016/j.bmc.2008.02.033]

16. 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]

17. Kier LB, Hall LH..  (1977)  Structure-activity studies on hallucinogenic amphetamines using molecular connectivity.,  20  (12): [PMID:592329] [10.1021/jm00222a019]

18. Glennon RA, Liebowitz SM, Mack EC..  (1978)  Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues.,  21  (8): [PMID:278843] [10.1021/jm00206a022]

19. 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