CINNAMEDRINE

Possibly Marketed Outside US

Details

Stereochemistry	UNKNOWN
Molecular Formula	C19H23NO
Molecular Weight	281.392
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)C1=CC=CC=C1)N(C)C\C=C\C2=CC=CC=C2

InChI

InChIKey=YMJMZFPZRVMNCH-FMIVXFBMSA-N

InChI=1S/C19H23NO/c1-16(19(21)18-13-7-4-8-14-18)20(2)15-9-12-17-10-5-3-6-11-17/h3-14,16,19,21H,15H2,1-2H3/b12-9+

HIDE SMILES / InChI

Molecular Formula	C19H23NO
Molecular Weight	281.392
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3615570 | doi:10.1001/archinte.1982.00340210181040 Retrived from: http://jamanetwork.com/journals/jamainternalmedicine/article-abstract/602330

Cinnamedrine is an active ingredient of midol (a combination of cinnamedrine hydrochloride, aspirin, phenacetin, and caffeine) used to relieve dysmenorrhea. Midol was an over-the-counter drug, which was discontinued due to a marketing decision.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dysmenorrhea 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7103644	Primary		Not Provided 504	midol Approved Use Unknown

PubMed

Title	Date	PubMed
Cinnamedrine: potential for abuse.	1983 Mar	6887304
Antiarrhythmic-like actions of the smooth muscle spasmolytic agent, cinnamedrine, on action potentials of mammalian ventricular tissue.	1987	3615570

Patents

Sample Use Guides

In Vivo Use Guide

Midol (a combination of cinnamedrine hydrochloride, aspirin, phenacetin, and caffeine) - two tablets every four hours, with a maximum eight tablets per day.

Route of Administration: Oral

In Vitro Use Guide

It was examined influence of cinnamedrine on the smooth muscle relaxing properties using rat uterus. Cinnamedrine exhibited dose-related spasmolytic activity in the isolated spontaneously contracting rat uterus and in uterine tissue pretreated with oxytocin to augment spasms. The IC50's for cinnamedrine was 36.2 microM; the IC50's after oxytocin pretreatment was 25.7 microM for cinnamedrine.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:28:32 UTC 2023` Edited by `admin` on `Fri Dec 15 17:28:32 UTC 2023`
Record UNII	Y1245J8012
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CINNAMEDRINE

Official Name

English

cinnamedrine [INN]

Common Name

English

CINNAMEDRINE [USAN]

Common Name

English

BENZENEMETHANOL, .ALPHA.-(1-(METHYL(3-PHENYL-2-PROPENYL)AMINO)ETHYL)-

Systematic Name

English

α-[1-(Cinnamylmethylamino)ethyl]benzyl alcohol

Systematic Name

English

Cinnamedrine [WHO-DD]

Common Name

English

CINNAMEDRINE [MI]

Common Name

English

CINNAMEDRINE [VANDF]

Common Name

English

CINNAMEDRINE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C87053