4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-triene

ID: ALA1908323

Cas Number: 524713-56-2

PubChem CID: 5362449

Max Phase: Phase

Molecular Formula: C18H25NO

Molecular Weight: 271.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: L-methorphan | Levomethorphan solution | IDS-NL-004 | IDS-NL-005 | Levomethorphan|l-Methorphan|Methorphan|125-70-2|Levomethorphane|Levometorfano|Levomethorphanum|(-)-3-Methoxy-N-methylmorphinan|Levometorfano [INN-Spanish]|Levomethorphane [INN-French]|Levomethorphanum [INN-Latin]|RACEMETHORPHAN|Racemethorphanum|Morphinan, 3-methoxy-17-methyl-, l-|7ZZ22K9QE6|8YB8F78WM1|IDS-NL-004|IDS-NL-005|Dextromethorfan [Czech]|Destrometerfano [DCIT]|Dextrometorphan|Racemethorphane|Racemetorfano|DextromethorphaShow More⌵

Canonical SMILES:  COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C)CC3

Standard InChI:  InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m0/s1

Standard InChI Key:  MKXZASYAUGDDCJ-CGTJXYLNSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -5.6571   -4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0696   -3.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8947   -3.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3072   -4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8947   -5.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0696   -5.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6571   -3.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8321   -3.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4196   -3.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8321   -4.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -3.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -4.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -5.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4196   -5.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4197   -2.3351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0352   -4.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8363   -2.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5274   -1.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9196   -2.8980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3071   -5.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8946   -6.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3322   -2.1836    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  1  2  2  0
 10  1  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 10  9  1  0
 10 14  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  1  0
 10 16  1  0
 15 17  1  0
 17 16  1  0
 15 18  1  0
  9 19  1  1
  5 20  1  0
 20 21  1  0
  8 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1908323

   LEVOMETHORPHAN

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: 271.40

Molecular Weight (Monoisotopic): 271.1936

AlogP: 3.38

#Rotatable Bonds: 1

Polar Surface Area: 12.47

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.85

CX LogP: 3.49

CX LogD: 1.08

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.78

Np Likeness Score: 1.15

References

1. Hernández-Gallegos Z, Lehmann PA..  (1990)  A Free-Wilson/Fujita-Ban analysis and prediction of the analgesic potency of some 3-hydroxy- and 3-methoxy-N-alkylmorphinan-6-one opioids.,  33  (10): [PMID:2213833] [10.1021/jm00172a021]

2. Berger ML, Schweifer A, Rebernik P, Hammerschmidt F..  (2009)  NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds.,  17  (9): [PMID:19345586] [10.1016/j.bmc.2009.03.025]

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

Source

Source(2):

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