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Prajmaline

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Also known as: Prajmalium, N-propylajmaline, 35080-11-6, 75934ud4gj, Ajmalanium, 17,21-dihydroxy-4-propyl-, (17r,21-alpha)-, N-propylajmalinium

Molecular Formula

C₂₃H₃₃N₂O₂+

Molecular Weight

369.5 g/mol

InChI Key

UAUHEPXILIZYCU-ALHOSYKFSA-N

FDA UNII

75934UD4GJ

A derivative of the rauwolfia alkaloid AJMALINE. It is an anti-arrhythmia agent but may cause liver damage.

1 2D Structure

Prajmaline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,9R,10S,12R,13S,14R,15R,16S,17S,18R)-13-ethyl-8-methyl-15-propyl-8-aza-15-azoniahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-14,18-diol

2.1.2 InChI

InChI=1S/C23H33N2O2/c1-4-10-25-17-11-14(13(5-2)22(25)27)19-18(25)12-23(21(19)26)15-8-6-7-9-16(15)24(3)20(17)23/h6-9,13-14,17-22,26-27H,4-5,10-12H2,1-3H3/q+1/t13-,14-,17-,18-,19-,20-,21+,22+,23+,25-/m0/s1

2.1.3 InChI Key

UAUHEPXILIZYCU-ALHOSYKFSA-N

2.1.4 Canonical SMILES

CCC[N+]12C3CC(C(C1O)CC)C4C2CC5(C3N(C6=CC=CC=C65)C)C4O

2.1.5 Isomeric SMILES

CCC[N@@+]12[C@H]3C[C@@H]([C@@H]([C@H]1O)CC)[C@H]4[C@@H]2C[C@@]5([C@H]3N(C6=CC=CC=C65)C)[C@@H]4O

2.2 Other Identifiers

2.2.1 UNII

75934UD4GJ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bitartrate, Prajmaline

2. Bitartrate, Prajmalium

3. N-propylajmaline

4. Neo Gilurytmal

5. Neo-gilurytmal

6. Neogilurytmal

7. Prajmaline Bitartrate

8. Prajmalium

9. Prajmalium Bitartrate

2.3.2 Depositor-Supplied Synonyms

1. Prajmalium

2. N-propylajmaline

3. 35080-11-6

4. 75934ud4gj

5. Ajmalanium, 17,21-dihydroxy-4-propyl-, (17r,21-alpha)-

6. N-propylajmalinium

7. Prajmalium Ion

8. Prajmalium Cation

9. Prajmalum

10. N(sup 4)-propylajmalinium

11. Unii-75934ud4gj

12. Prajmaline [mi]

13. Prajmalium [who-dd]

14. (17r,21-alpha)-17,21-dihydroxy-4-propylajmalanium

15. Chebi:135560

16. Zinc252462538

17. Db13555

18. Q7238143

19. Ajmalanine, 17,21-dihydroxy-4-propyl-, (17r,21.alpha.)-

20. (1r,9r,10s,12r,13s,14r,15r,16s,17s,18r)-13-ethyl-8-methyl-15-propyl-8-aza-15-azoniahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-14,18-diol

2.4 Create Date

2014-08-25

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₃N₂O₂+
Molecular Weight	369.5 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	369.254203300 g/mol
Monoisotopic Mass	369.254203300 g/mol
Topological Polar Surface Area	43.7 Å²
Heavy Atom Count	27
Formal Charge	1
Complexity	642
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

4.2 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01B - Antiarrhythmics, class i and iii

C01BA - Antiarrhythmics, class ia

C01BA08 - Prajmaline

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