RESCINNAMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H42N2O9
Molecular Weight	634.716
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@@H](OC(=O)\C=C\C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]4([H])N(CCC5=C4NC6=C5C=CC(OC)=C6)C2

InChI

InChIKey=SZLZWPPUNLXJEA-QEGASFHISA-N

InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13284667|http://pubs.acs.org/doi/abs/10.1021/ja01639a079

Rescinnamine is an alkaloid isolated from Rauvolfia serpentina and approved by FDA for the treatment of hypertension. The mechanism of rescinnamine is not established, but probably resembles that of reserpine. Rescinnamine approval was discontinued by unknown reason.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonergic synapse 2 Target ID: map04726 Sources: ISBN-13: 978-0553763126, Kenneth H., 'Overcoming Hypertension: Preventive Medicine Program' (2012), Retrieved from \| https://books.google.es/books?id=guP-e8igrK0C&dq	Inhibitor 8297
Dopaminergic synapse 2 Target ID: map04728 Sources: ISBN-13: 978-0553763126, Kenneth H., 'Overcoming Hypertension: Preventive Medicine Program' (2012), Retrieved from \| https://books.google.es/books?id=guP-e8igrK0C&dq	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm173134.htm	Primary		Approved 8429	MODERIL Approved Use High blood preasure. Launch Date -4.15583994E11

Doses

Dose	Population	Adverse events
15 mg single, parenteral Highest studied dose Dose: 15 mg Route: parenteral Route: single Dose: 15 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13313540	unhealthy n = 3 Health Status: unhealthy Condition: hypertension Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/13313540	Other AEs: Weakness, Dizziness... Other AEs: Weakness Dizziness Nasal congestion Sources: https://pubmed.ncbi.nlm.nih.gov/13313540
4 mg 1 times / day multiple, oral Highest studied dose Dose: 4 mg, 1 times / day Route: oral Route: multiple Dose: 4 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13313540	unhealthy n = 10 Health Status: unhealthy Condition: hypertension Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/13313540	Sources: https://pubmed.ncbi.nlm.nih.gov/13313540

AEs

AE	Dose	Population
Dizziness	15 mg single, parenteral Highest studied dose Dose: 15 mg Route: parenteral Route: single Dose: 15 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13313540	unhealthy n = 3 Health Status: unhealthy Condition: hypertension Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/13313540
Nasal congestion	15 mg single, parenteral Highest studied dose Dose: 15 mg Route: parenteral Route: single Dose: 15 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13313540	unhealthy n = 3 Health Status: unhealthy Condition: hypertension Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/13313540
Weakness	15 mg single, parenteral Highest studied dose Dose: 15 mg Route: parenteral Route: single Dose: 15 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13313540	unhealthy n = 3 Health Status: unhealthy Condition: hypertension Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/13313540

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		binder 1

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461		P-gp 257

Drug as perpetrator

Target	Modality	Activity
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18310528/	yes [IC50 1.53 uM]
CYP2D6 1891	binder 7 Sources: https://pubmed.ncbi.nlm.nih.gov/31828069/	yes
P-gp 1650	binder 7 Sources: https://pubmed.ncbi.nlm.nih.gov/2567994/ \| https://pubmed.ncbi.nlm.nih.gov/1967551/	yes
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/7476894/	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-4488	http://www.3bsc.com/index/pro_info.php?id=79428
AHH Chemical co.,ltd	MT-58416	http://www.ahhchemical.com/product/MT-58416.html
Aurora Fine Chemicals LLC	A24.067.386	http://online.aurorafinechemicals.com/info?ID=A24.067.386
Aurora Fine Chemicals LLC	K05.570.460	http://online.aurorafinechemicals.com/info?ID=K05.570.460
ChemFaces	CFN92580	http://www.chemfaces.com/natural/Reserpinine-CFN92580.html
ChemMol	99053594	http://www.chemmol.com/chemmol/99053594.html
Chemspace	CSSS00116207468	https://chem-space.com/CSSS00116207468
LGC Standards	LGCFOR1941.00	https://www.lgcstandards.com/US/en/p/LGCFOR1941.00
Lab Network	LN01808479	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01808479
MuseChem	R029497	https://www.musechem.com/product/R029497.html
Smolecule	S724634	https://www.smolecule.com/products/s724634
eNovation Chemicals	D672372	https://www.enovationchem.com/ProductDetails.asp?ProductID=D672372

PubMed

Title	Date	PubMed
A structure-function relationship among reserpine and yohimbine analogues in their ability to increase expression of mdr1 and P-glycoprotein in a human colon carcinoma cell line.	1995 Oct	7476894
Small molecules targeting severe acute respiratory syndrome human coronavirus.	2004 Jul 6	15226499
Search of chemical scaffolds for novel antituberculosis agents.	2005 Apr	15809316

Patents

Sample Use Guides

In Vivo Use Guide

From 1 to 2 mg of rescinnamine are given orally.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

RESCINNAMINE

Official Name

English

RESEALOID

Brand Name

English

RESERPININE

Common Name

English

3,4,5-TRIMETHOXYCINNAMIC ACID ESTER OF METHYL RESERPATE

Common Name

English

MODERIL

Brand Name

English

METHYL 18.BETA.-HYDROXY-11,17.ALPHA.-DIMETHOXY-3.BETA.,20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLATE

Common Name

English

RESCINNAMINE [VANDF]

Common Name

English

APOTERIN S

Common Name

English

Rescinnamine [WHO-DD]

Common Name

English

CARTRIC

Brand Name

English

METHYL 3,4,5-TRIMETHOXYCINNAMOYL RESERPATE

Common Name

English

RESCINNAMINE [JAN]

Common Name

English

CINNALOID

Brand Name

English

RESCINNAMINE [MART.]

Common Name

English

SCINNAMINA

Brand Name

English

RESCISAN

Brand Name

English

RESCINNAMINE [ORANGE BOOK]

Common Name

English

rescinnamine [INN]

Common Name

English

TSURUSELPI S

Brand Name

English

RESCINNAMINE [MI]

Common Name

English

(3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-11,17-DIMETHOXY-18-(((2E)-1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPEN-1-YL)OXY)-YOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER

Common Name

English

NSC-15628

Code

English

RESCINNAMINE [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C270