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Details

Stereochemistry ACHIRAL
Molecular Formula C10H20O2.H2O
Molecular Weight 190.2799
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERPIN HYDRATE

SMILES

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

InChI

InChIKey=JGKJMBOJWVAMIJ-OFAZAQPOSA-N
InChI=1S/C10H20O2.H2O/c1-9(2,11)8-4-6-10(3,12)7-5-8;/h8,11-12H,4-7H2,1-3H3;1H2/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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
PMD, a registered botanical mosquito repellent with deet-like efficacy.
2006 Sep
A low-cost repellent for malaria vectors in the Americas: results of two field trials in Guatemala and Peru.
2007 Aug 1
Limitation of using synthetic human odours to test mosquito repellents.
2009 Jul 7
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
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 15:03:14 UTC 2023
Edited
by admin
on Fri Dec 15 15:03:14 UTC 2023
Record UNII
S3V868548T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TERPIN HYDRATE
MART.   USP   USP-RS   VANDF   WHO-DD  
Common Name English
TERPIN MONOHYDRATE [EP MONOGRAPH]
Common Name English
P-MENTHANE-1,8-DIOL MONOHYDRATE
Systematic Name English
TERPINOL HYDRATE
Common Name English
TERPIN HYDRATE [MART.]
Common Name English
TERPINENE HYDRATE
Systematic Name English
CIS-TERPIN HYDRATE
Common Name English
CYCLOHEXANEMETHANOL, 4-HYDROXY-.ALPHA.,.ALPHA.,4-TRIMETHYL-, HYDRATE (1:1), CIS-
Common Name English
TERPIN MONOHYDRATE
Common Name English
P-MENTHANE-1,8-DIOL, MONOHYDRATE
Systematic Name English
NSC-760418
Code English
CIS-P-METHANE-1,8-DIOL MONOHYDRATE
Common Name English
TERPIN HYDRATE [USP-RS]
Common Name English
TERPIN HYDRATE [VANDF]
Common Name English
TERPIN CIS-FORM HYDRATE
MI  
Common Name English
CYCLOHEXANEMETHANOL, 4-HYDROXY-.ALPHA.,.ALPHA.,4-TRIMETHYL-, MONOHYDRATE
Systematic Name English
TERPIN CIS-FORM HYDRATE [MI]
Common Name English
Terpin hydrate [WHO-DD]
Common Name English
TERPIN HYDRATE [USP MONOGRAPH]
Common Name English
Code System Code Type Description
RS_ITEM_NUM
1644003
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
EVMPD
SUB15488MIG
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID00947401
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
FDA UNII
S3V868548T
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
RXCUI
89916
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY RxNorm
MERCK INDEX
m10581
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY Merck Index
SMS_ID
100000087177
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
DRUG BANK
DB13163
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
CAS
2451-01-6
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
NSC
760418
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL1651998
Created by admin on Fri Dec 15 15:03:14 UTC 2023 , Edited by admin on Fri Dec 15 15:03:14 UTC 2023
PRIMARY
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