NAPELLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H33NO3
Molecular Weight	359.5023
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12[C@@H]3C[C@H]4[C@@]1([C@@H](O)CC[C@@]4(C)CN2CC)[C@]5([H])C[C@H](O)[C@@H]6C[C@]35[C@H](O)C6=C

InChI

InChIKey=AZAZKLKDEOMJBJ-AFJRDBIPSA-N

InChI=1S/C22H33NO3/c1-4-23-10-20(3)6-5-17(25)22-15(20)7-13(18(22)23)21-9-12(11(2)19(21)26)14(24)8-16(21)22/h12-19,24-26H,2,4-10H2,1,3H3/t12-,13+,14+,15-,16-,17+,18-,19-,20+,21+,22+/m1/s1

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Description
Sources: http://www.latoxan.net/details-napelline+for+research+and+life+sciences-193.html | https://www.ncbi.nlm.nih.gov/pubmed/25110090 | https://www.ncbi.nlm.nih.gov/pubmed/24770754 | http://www.funakoshi.co.jp/data/datasheet/LAT/L6215.pdf

Napelline is a diterpenoid alkaloid, from plants of the Aconitum genus, Ranunculaceae. It is a potent antiarrhythmic of class I with weak hypotensive and N-cholinoblocking effects. Napelline has analgesic and anti-inflammatory activity. Napelline has a stronger antiarrhythmic activity than Quinidine or Procaïnamide. 10(-4) - 10(-5) M block inward Na+ currents

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
sodium channel activity 16 Target ID: GO:0005272 Sources: http://www.funakoshi.co.jp/data/datasheet/LAT/L6215.pdf	Blocker 537

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25110090	Primary	Preclinical	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24770754	Primary	Preclinical	Unknown Approved Use Unknown
Arrhythmia 38 Sources: https://link.springer.com/article/10.1007/BF02291540	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
SELENIUM DEHYDROGENATION OF NAPELLINE.	1938 Feb 11	17743000
Analgesic activity of diterpene alkaloids from Aconitum baikalensis.	2014 Aug	25110090
Anti-inflammatory activity of diterpene alkaloids from Aconitum baikalense.	2014 Mar	24770754

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Napelline (0.025 mg/kg) exhibited an analgesic effect in the acetylcholine cramps model by prolonging the time before manifestation of the nociceptive reaction and reducing the number of cramps.

Route of Administration: Intravenous

In Vitro Use Guide

Napelline in a concentration of 50 nM in vitro significantly increased the number of CFU-F formation from bone marrow cells of mice in comparison with the basal level.

Name

Type

Language

NAPELLINE

Common Name

English

NAPELLINE [MI]

Common Name

English

12,3,6A-ETHANYLYLIDENE-9,11A-METHANOAZULENO(2,1-B)AZOCINE-6,8,11-TRIOL, 1-ETHYLTETRADECAHYDRO-3-METHYL-10-METHYLENE-,(3R,6S,6AR,6BR,8S,9R,11R,11AR,12R,12AR,14R)-

Common Name

English

7,20-CYCLOVEATCHANE-1,12,15-TRIOL, 21-ETHYL-4-METHYL-16-METHYLENE-, (1-.ALPHA.,12-.ALPHA., 15-.BETA.)-

Common Name

English

LUCICULINE

Common Name

English

Code System Code Type Description

CAS

5008-52-6