ADIPHENINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H25NO2.ClH
Molecular Weight	347.879
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCN(CC)CCOC(=O)C(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=LKPINBXAWIMZCG-UHFFFAOYSA-N

InChI=1S/C20H25NO2.ClH/c1-3-21(4-2)15-16-23-20(22)19(17-11-7-5-8-12-17)18-13-9-6-10-14-18;/h5-14,19H,3-4,15-16H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula	C20H25NO2
Molecular Weight	311.418
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: Aronson, K. (2015) Meyler's Side Effects of Drugs, page 85, retrieved from: https://books.google.ru/books?id=NOKoBAAAQBAJ | http://www.rusmedserv.com/lekarstva/spazmolitin.html | https://www.ncbi.nlm.nih.gov/pubmed/14038458

Adiphenine is a ternary amino ligand. It is used as a local anesthetic that reduces the frequency of acetylcholine-induced single-channel currents. It was originally introduced as a spasmolytic agent. Adiphenine reduced the muscle tone of the gastrointestinal tract, bile duct and gallbladder, bronchi, bladder. It affects the tone of the muscles of the eye, causing the pupil dilated (mydriasis), increased intraocular pressure, and paralysis of accommodation. Influences on the cardiovascular system, causing tachycardia and improving AV-conduction. Adiphenine side effects are: nausea, vomiting, heartburn, dizziness, headache. Adiphenine has not been widely used clinically.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nicotinic acetylcholine receptor alpha1/beta1/epsilon/delta 14 Target ID: CHEMBL3137264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391	Inhibitor 8504
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL1907609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3404446	Inhibitor 8504		198.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Spasm 18 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15435188 https://www.ncbi.nlm.nih.gov/pubmed/14353164 https://www.ncbi.nlm.nih.gov/pubmed/13977229	Primary		Withdrawn	Trasentine Approved Use Adiphenine is indicated for the treatment of spasms of smooth muscles of the digestive tract, bile ducts, bronchi.
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391	Primary		Withdrawn	Trasentine Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 550 CYP1A2 2153 CYP2C19 2057 OATP1B1 1079 OATP1B3 961

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	no [Activation >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	no [Activation >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzUzODQ2In19	no [Activation >10 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	yes [Activation 5.01187 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzUzODQ2In19	yes [Activation 5.01187 uM]
BSEP 554	inhibitor 4027 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50395519, https://pubmed.ncbi.nlm.nih.gov/22961681/	yes [IC50 158.4 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1NTY1NCJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1NTY1NCJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY564988	https://www.001chemical.com/chem/64-95-9
Ambinter	Amb1866835	http://www.ambinter.com/reference/1866835
Aurora Fine Chemicals LLC	K02.237.239	http://online.aurorafinechemicals.com/info?ID=K02.237.239
BLD Pharm	BD01303012	http://www.bldpharm.com/products/64-95-9.html
BOC Sciences	64-95-9	https://www.bocsci.com/2-diethylaminoethyl-2-2-di-phenyl-acetate-cas-64-95-9-item-130836.html
ChemMol	49409913	http://www.chemmol.com/chemmol/49409913.html
Chemspace	CSSS00046194224	https://chem-space.com/CSSS00046194224
mcule	MCULE-6767246073	https://mcule.com/MCULE-6767246073/
Molcore	MC564988	https://www.molcore.com/product/64-95-9
MolPort	MolPort-002-579-049	https://www.molport.com/shop/molecule-link/MolPort-002-579-049
Smolecule	S517271	http://www.smolecule.com/products/s517271
THE BioTek	bt-258061	https://www.thebiotek.com/product/inhibitors/bt-258061
Yuhao Chemical	XJ0042	http://www.chemyuhao.com/64-95-9.html

PubMed

Title	Date	PubMed
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015-01-05	25455453
The chemical basis of pharmacology.	2010-12-07	21058655
Could chiropractors screen for adverse drug events in the community? Survey of US chiropractors.	2010-11-17	21083911
The haunting of medical journals: how ghostwriting sold "HRT".	2010-09-07	20838656
Legal remedies for medical ghostwriting: imposing fraud liability on guest authors of ghostwritten articles.	2010-08	21829331
Desvenlafaxine in major depressive disorder: an evidence-based review of its place in therapy.	2010-06-15	20694066
Negotiating the boundary between medicine and consumer culture: online marketing of nutrigenetic tests.	2010-03	20022680
Of sophists and spin-doctors: industry-sponsored ghostwriting and the crisis of academic medicine.	2010-01	21327175
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Planning Future Strategies for Domestic and International NeuroAIDS Research, July 24-25, 2008.	2009-09	19455426
The local anaesthetics proadifen and adiphenine inhibit nicotinic receptors by different molecular mechanisms.	2009-07	19422391
Improving introspection to inform free will regarding the choice by healthy individuals to use or not use cognitive enhancing drugs.	2009-06-16	19531231
Sequestered evidence and the distortion of clinical practice guidelines.	2009	19395820
[The anxyolytic effect of mild hypobaric hypoxia in a model of post-traumatic stress disorder in rats].	2008-10-02	18825947
(3S,4R)-4-(4-Fluoro-phen-yl)-3-(hydroxy-meth-yl)piperidinium chloride.	2008-04-04	21202292
Paroxetine.	2008-04	18345955
Nutritional therapies for mental disorders.	2008-01-21	18208598
Trial registration for public trust: making the case for medical devices.	2008-01	18095047
Generic entry, reformulations and promotion of SSRIs in the US.	2008	18563951
Paroxetine versus placebo and other agents for depressive disorders: a systematic review and meta-analysis.	2007-12	18162015
Prevalence and predictors of antidepressant use in a cohort of pregnant women.	2007-09	17565615
Paroxetine and congenital malformations: meta-Analysis and consideration of potential confounding factors.	2007-05	17697910
Urticarial vasculitis secondary to paroxetine.	2007-03-22	17373154
Patterns of prescription and self-medication for treating primary dysmenorrhea in a Mexican population.	2007	18605257
Rare case of serotonin syndrome with therapeutic doses of paroxetine.	2006-11-24	17122538
Effect of generic-only drug benefits on seniors' medication use and financial burden.	2006-09	16961441
There is no such thing as a psychiatric disorder/disease/chemical imbalance.	2006-07	16848623
Paxil and the risk of birth defects.	2006-05-05	16673451
[Selective serotonin reuptake inhibitors (SSRIs) in pregnancy].	2006-04-12	16686331
Paxil: part of the process.	2006-04	16628835
Disease mongering in drug promotion: do governments have a regulatory role?	2006-04	16597181
What are the public health effects of direct-to-consumer drug advertising?	2006-03	16563041
The SSRI trials in children: disturbing implications for academic medicine.	2006	16862717
Serotonin and depression: a disconnect between the advertisements and the scientific literature.	2005-12	16268734
Medicine as a corporate enterprise, patient welfare centered profession, or patient welfare centered professional enterprise?	2005-11	22679354
Damming the flow of drugs into drinking water.	2005-10	16203229
Manufacturing violations prompt seizure of Paxil CR, Avandamet.	2005-09-01	16130202
[Clinical effects of paxil in poststroke rehabilitation].	2005	15704483
A taxpayer-funded clinical trials registry and results database.	2004-12	15562322
Antidepressant medication use among First Nations peoples residing within British Columbia.	2004-11-05	15536588
Acute and chronic toxicity of five selective serotonin reuptake inhibitors in Ceriodaphnia dubia.	2004-09	15379001
Environmental risk assessment of paroxetine.	2004-06-15	15260335
Medicalization, markets and consumers.	2004	15779472
Concerns about Paxil for children.	2003-12-12	14666887
Adolescents searching for health information on the Internet: an observational study.	2003-10-17	14713653
Causality and collateral estoppel: process and content of recent SSRI litigation.	2003	14584540
Serotonin reuptake inhibitor (Paxil) does not prevent the vasovagal reaction associated with carotid sinus massage and/or lower body negative pressure in healthy volunteers.	2002-09-17	12234955
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.	2001-12	11714893
New use for Paxil approved.	2001-11-06	11692882
[Effect of several neuroleptic, adreno-, sympatho- and cholinolytic substances on the development of experimental cerebral edema induced by nicotine].	1977-05-01	20324

Patents

Sample Use Guides

In Vivo Use Guide

50-100 mg 2-3-4 times per day. Course of treatment - 3-4 weeks.

Route of Administration: Oral

In Vitro Use Guide

Adiphenine decreased the frequency of ACh-induced single-channel currents. Adiphenine decreased cluster duration (36-fold at 100 uM x L(-1)). Preincubation with adiphenine did not change amplitude but increased the decay rate (IC(50)= 15 uM x L(-1)).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:52:13 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:13 GMT 2025`
Record UNII	42B4PDY0AV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADIPHENINE HYDROCHLORIDE [MI]

Preferred Name

English

ADIPHENINE HYDROCHLORIDE

Official Name

English

NSC-129224

Code

English

2-(Diethylamino)ethyl diphenylacetate hydrochloride

Systematic Name

English

ADIPHENINE HYDROCHLORIDE [MART.]

Common Name

English

Adiphenine hydrochloride [WHO-DD]

Common Name

English

BENZENEACETIC ACID, .ALPHA.-PHENYL-2-(DIETHYLAMINO)ETHYL ESTER HYDROCHLORIDE

Common Name

English

ADIPHENINE HYDROCHLORIDE [USAN]

Common Name

English

ADIPHENINE HCL

Common Name

English

TRASENTINE

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704