2-(3,4,5-Trimethoxy-phenyl)-ethylamine

ID: ALA26687

Cas Number: 54-04-6

PubChem CID: 4076

Max Phase: Phase

Molecular Formula: C11H17NO3

Molecular Weight: 211.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-(3,4,5-Trimethoxyphenyl)Ethanamine | M (psychedelic) | Mescaline | NSC-30419 | mescaline|Mescalin|Tmpea|3,4,5-Trimethoxyphenethylamine|Mezcaline|54-04-6|2-(3,4,5-Trimethoxyphenyl)ethanamine|3,4,5-Trimethoxybenzeneethanamine|3,4,5-Trimethoxyphenylethylamine|mescalina|mezcalina|Meskalin|Mezcalin|Benzeneethanamine, 3,4,5-trimethoxy-|Phenethylamine, 3,4,5-trimethoxy-|NSC 30419|Mescline|Mezcline|Ethane, 1-amino-2-(3,4,5-trimethoxyphenyl)-|2-(3,4,5-trimethoxy-phenyl)-ethylamine|EINECS 200-190-7|UNIIShow More⌵

Canonical SMILES:  COc1cc(CCN)cc(OC)c1OC

Standard InChI:  InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

Standard InChI Key:  RHCSKNNOAZULRK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331    3.6060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -3.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  2  0
  2  5  1  0
  4  6  1  0
  5  6  2  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
  6 11  1  0
 10 12  1  0
 11 12  1  0
  7 13  1  0
  9 14  1  0
  8 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA26687

   MESCALINE

2. Alternative Forms:

   

   ALA26687

   Mescaline hydrochloride

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 211.26

Molecular Weight (Monoisotopic): 211.1208

AlogP: 1.21

#Rotatable Bonds: 5

Polar Surface Area: 53.71

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.77

CX LogP: 0.91

CX LogD: -1.37

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.80

Np Likeness Score: 0.52

References

1. Jacob P, Shulgin AT..  (1981)  Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline.,  24  (11): [PMID:7310812] [10.1021/jm00143a017]

2. Andrews PR, Craik DJ, Martin JL..  (1984)  Functional group contributions to drug-receptor interactions.,  27  (12): [PMID:6094812] [10.1021/jm00378a021]

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

4. Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE..  (1997)  Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives.,  40  (19): [PMID:9301661] [10.1021/jm970219x]

5. Chambers JJ, Parrish JC, Jensen NH, Kurrasch-Orbaugh DM, Marona-Lewicka D, Nichols DE..  (2003)  Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.,  46  (16): [PMID:12877591] [10.1021/jm030064v]

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. Jacob P, Shulgin AT..  (1984)  Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues.,  27  (7): [PMID:6737431] [10.1021/jm00373a013]

9. McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE..  (2006)  C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor.,  49  (14): [PMID:16821786] [10.1021/jm060272y]

10. 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]

11. 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]

12. Jacob P, Anderson G, Meshul CK, Shulgin AT, Castagnoli N..  (1977)  Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane.,  20  (10): [PMID:903913] [10.1021/jm00220a001]

13. Nichols DE, Dyer DC..  (1977)  Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues.,  20  (2): [PMID:836502] [10.1021/jm00212a022]

14. 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]

15. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates