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Details

Stereochemistry ACHIRAL
Molecular Formula C10H20O2
Molecular Weight 172.2646
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERPIN

SMILES

CC(C)(O)[C@H]1CC[C@@](C)(O)CC1

InChI

InChIKey=RBNWAMSGVWEHFP-WAAGHKOSSA-N
InChI=1S/C10H20O2/c1-9(2,11)8-4-6-10(3,12)7-5-8/h8,11-12H,4-7H2,1-3H3/t8-,10+

HIDE SMILES / InChI

Molecular Formula C10H20O2
Molecular Weight 172.2646
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created using several sources including: http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?fr=310.545 http://www.fda.gov/regulatoryinformation/dockets/ucm113857.htm; https://www.drugs.com/uk/pdf/leaflet/849432.pdf; https://www.ncbi.nlm.nih.gov/pubmed/?term=19557607; https://www.ncbi.nlm.nih.gov/pubmed/?term=19551736

Terpin hydrate is an expectorant commonly used to loosen mucus in patients presenting with acute or chronic bronchitis, and related conditions. Terpin is derived from oil of turpentine, oregano, thyme and eucalyptus. In 1855 Lepin who first investigated terpin reported that it acted upon the mucous membranes and also the nervous system in a manner similar to the oil of turpentine. Terpin hydrate was available in the USA in 1907 in the preparations such as Elixir of Terpin Hydrate alone or in combination with codein or heroin as an antitussives. It was banned by the U.S. Food and Drug Administration (FDA) in the 1990s due to lack of proof of efficacy but is a medicine available in a number of countries worldwide commonly used in combination with codein. At present it is FDA approved for as an OTC use in combination formulations (with acetaminophen and other drugs) used as internal analgesics. Terpin was recently introduced as a natural topical insect repellent.

Originator

Curator's Comment: Terpin hydrate was first physiologically investigated by Lepine in 1855.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TERPIN AND CODEINE LINCTUS

Approved Use

For symptomatic relief of troublesome coughs.
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Field evaluation of three plant-based insect repellents against malaria vectors in Vaca Diez Province, the Bolivian Amazon.
2002 Jun
Repellent activities of stereoisomers of p-menthane-3,8-diols against Anopheles gambiae (Diptera: Culicidae).
2002 Sep
Enhancement effect of p-menthane-3,8-diol on in vitro permeation of antipyrine and indomethacin through Yucatan micropig skin.
2004 Jul
Repellency of MyggA Natural spray (para-menthane-3,8-diol) and RB86 (neem oil) against the tick Ixodes ricinus (Acari: Ixodidae) in the field in east-central Sweden.
2006
A low-cost repellent for malaria vectors in the Americas: results of two field trials in Guatemala and Peru.
2007 Aug 1
Fragrance material review on geranodyle.
2008 Nov
Percutaneous absorption of an insect repellent p-menthane-3,8-DIOL: a model for human dermal absorption.
2009
Limitation of using synthetic human odours to test mosquito repellents.
2009 Jul 7
Effective insect repellent formulation in both surfactantless and classical microemulsions with a long-lasting protection for human beings.
2009 Jun
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
tert-Butyl 6-bromo-1,4-dimethyl-9H-carbazole-9-carboxyl-ate.
2010 Jul 10
Patents

Sample Use Guides

Adults: Take 1 x 5ml (32.5 mg terpin hydrate) spoonful, diluted with water, after food. Repeat after 6 hours if required, but not more than 3 doses in 24 hours. The elderly: Ask your doctor for advice. A lower dose may be more suitable. Do not give to children under 18 years old
Route of Administration: Oral
The enhancing effect of p-Menthane-3,8-diol on skin permeation of antipyrine and indomethacin through Yucatan micropig skin was studied. p-Menthane-3,8-diol partitioned to the skin relatively high concentrations of 5.9 mg/ cm^3.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:46:10 UTC 2023
Edited
by admin
on Fri Dec 15 15:46:10 UTC 2023
Record UNII
MPF495B08R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TERPIN
MI   WHO-DD  
Common Name English
TERPIN [MI]
Common Name English
Terpin [WHO-DD]
Common Name English
NSC-403856
Code English
P-MENTHANE-1,8-DIOL
Systematic Name English
CIS-P-MENTHAN-1,8-DIOL
Common Name English
CYCLOHEXANEMETHANOL, 4-HYDROXY-.ALPHA.,.ALPHA.,4-TRIMETHYL-
Systematic Name English
CIS-1,8-P-MENTHANEDIOL
Common Name English
CYCLOHEXANEMETHANOL, 4-HYDROXY-.ALPHA.,.ALPHA.,4-TRIMETHYL-, CIS-
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL1651998
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
DRUG CENTRAL
2604
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
WIKIPEDIA
Terpin
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
CAS
565-48-0
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
209-279-5
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
SMS_ID
100000079907
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
NSC
403856
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
EVMPD
SUB16107MIG
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
CAS
80-53-5
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
ECHA (EC/EINECS)
201-288-2
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
ALTERNATIVE
FDA UNII
MPF495B08R
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY
MERCK INDEX
m10581
Created by admin on Fri Dec 15 15:46:10 UTC 2023 , Edited by admin on Fri Dec 15 15:46:10 UTC 2023
PRIMARY Merck Index
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT