ID: ALA6731

Max Phase: Phase

Molecular Formula: C10H13NO2

Molecular Weight: 179.22

Molecule Type: Small molecule

Representations

Synonyms (5): Mda (psychedelic) | Methylene dioxyamphetamine | Tenamfetamine | EA-1299 | SKF-5
Synonyms from Alternative Forms(5):

Canonical SMILES:  CC(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

Standard InChI Key:  NGBBVGZWCFBOGO-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: 179.22

Molecular Weight (Monoisotopic): 179.0946

AlogP: 1.31

#Rotatable Bonds: 2

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: 10.01

CX LogP: 1.43

CX LogD: -1.05

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.74

Np Likeness Score: 0.28

References

1. Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE..  (1998)  Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA).,  41  (6): [PMID:9526575] [10.1021/jm9705925]

2. 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]

3. 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]

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

5. Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE..  (1993)  Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine.,  36  (23): [PMID:8246240] [10.1021/jm00075a027]

6. 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]

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

8. 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]

9. 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]

10. Cloonan SM, Keating JJ, Butler SG, Knox AJ, Jørgensen AM, Peters GH, Rai D, Corrigan D, Lloyd DG, Williams DC, Meegan MJ..  (2009)  Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.,  44  (12): [PMID:19717215] [10.1016/j.ejmech.2009.07.027]

11. Cloonan SM, Keating JJ, Corrigan D, O'Brien JE, Kavanagh PV, Williams DC, Meegan MJ..  (2010)  Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.,  18  (11): [PMID:20466553] [10.1016/j.bmc.2010.04.022]

12. McNamara YM, Cloonan SM, Knox AJ, Keating JJ, Butler SG, Peters GH, Meegan MJ, Williams DC..  (2011)  Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents.,  19  (3): [PMID:21227702] [10.1016/j.bmc.2010.11.054]

13. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

14. Noorizadeh H, Noorizadeh M, Farmany A.  (2012)  Advanced QSRR models of toxicological screening of basic drugs in whole blood by UPLC-TOFMS,  21  (12): [10.1007/s00044-012-9977-1]

15. Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S..  (2013)  An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'.,  23  (11): [PMID:23602445] [10.1016/j.bmcl.2013.03.066]

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

17. Nichols DE, Kostuba LJ..  (1979)  Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.,  22  (10): [PMID:513074] [10.1021/jm00196a022]

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]

20. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names