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	ClH
Molecular Weight	36.461
Charge	0
Count

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

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

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 13 Target ID: CHEMBL3137264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391	Inhibitor 8297
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL1907609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3404446	Inhibitor 8297		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https://www.ncbi.nlm.nih.gov/pubmed/14353164 https://www.ncbi.nlm.nih.gov/pubmed/13977229	Primary		Withdrawn	Trasentine Approved Use Adiphenine is indicated for the treatment of spasms of smooth muscles of the digestive tract, bile ducts, bronchi.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 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391	Primary		Withdrawn	Trasentine Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 402 CYP1A2 1524 CYP2C19 1478 OATP1B1 788 OATP1B3 706

Drug as perpetrator

Target	Modality	Activity
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	no [Activation >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	no [Activation >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzUzODQ2In19	no [Activation >10 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	yes [Activation 5.01187 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzUzODQ2In19	yes [Activation 5.01187 uM]
BSEP 403	inhibitor 3277 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 803	inhibitor 3277 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 715	inhibitor 3277 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
MolPort	MolPort-002-579-049	https://www.molport.com/shop/molecule-link/MolPort-002-579-049
Molcore	MC564988	https://www.molcore.com/product/64-95-9
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
mcule	MCULE-6767246073	https://mcule.com/MCULE-6767246073/

PubMed

Title	Date	PubMed
[Effect of several neuroleptic, adreno-, sympatho- and cholinolytic substances on the development of experimental cerebral edema induced by nicotine].	1977 May-Jun	20324
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.	2001 Dec	11714893
New use for Paxil approved.	2001 Jul-Aug	11692882
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 Sep 17	12234955
Causality and collateral estoppel: process and content of recent SSRI litigation.	2003	14584540
Adolescents searching for health information on the Internet: an observational study.	2003 Oct 17	14713653
Concerns about Paxil for children.	2003 Sep-Oct	14666887
Medicalization, markets and consumers.	2004	15779472
A taxpayer-funded clinical trials registry and results database.	2004 Dec	15562322
Environmental risk assessment of paroxetine.	2004 Jun 15	15260335
Antidepressant medication use among First Nations peoples residing within British Columbia.	2004 Nov 5	15536588
Acute and chronic toxicity of five selective serotonin reuptake inhibitors in Ceriodaphnia dubia.	2004 Sep	15379001
[Clinical effects of paxil in poststroke rehabilitation].	2005	15704483
Serotonin and depression: a disconnect between the advertisements and the scientific literature.	2005 Dec	16268734
Manufacturing violations prompt seizure of Paxil CR, Avandamet.	2005 May-Jun	16130202
Medicine as a corporate enterprise, patient welfare centered profession, or patient welfare centered professional enterprise?	2005 Nov	22679354
Damming the flow of drugs into drinking water.	2005 Oct	16203229
Paxil: part of the process.	2006 Apr	16628835
Disease mongering in drug promotion: do governments have a regulatory role?	2006 Apr	16597181
[Selective serotonin reuptake inhibitors (SSRIs) in pregnancy].	2006 Apr 12	16686331
There is no such thing as a psychiatric disorder/disease/chemical imbalance.	2006 Jul	16848623
What are the public health effects of direct-to-consumer drug advertising?	2006 Mar	16563041
Paxil and the risk of birth defects.	2006 Mar-Apr	16673451
Urticarial vasculitis secondary to paroxetine.	2006 Nov-Dec	17373154
Rare case of serotonin syndrome with therapeutic doses of paroxetine.	2006 Nov-Dec	17122538
Effect of generic-only drug benefits on seniors' medication use and financial burden.	2006 Sep	16961441
The SSRI trials in children: disturbing implications for academic medicine.	2006 Spring	16862717
Patterns of prescription and self-medication for treating primary dysmenorrhea in a Mexican population.	2007	18605257
Paroxetine versus placebo and other agents for depressive disorders: a systematic review and meta-analysis.	2007 Dec	18162015
Paroxetine and congenital malformations: meta-Analysis and consideration of potential confounding factors.	2007 May	17697910
Prevalence and predictors of antidepressant use in a cohort of pregnant women.	2007 Sep	17565615
Generic entry, reformulations and promotion of SSRIs in the US.	2008	18563951
Paroxetine.	2008 Apr	18345955
(3S,4R)-4-(4-Fluoro-phen-yl)-3-(hydroxy-meth-yl)piperidinium chloride.	2008 Apr 4	21202292
Trial registration for public trust: making the case for medical devices.	2008 Jan	18095047
Nutritional therapies for mental disorders.	2008 Jan 21	18208598
[The anxyolytic effect of mild hypobaric hypoxia in a model of post-traumatic stress disorder in rats].	2008 Jul-Aug	18825947
The local anaesthetics proadifen and adiphenine inhibit nicotinic receptors by different molecular mechanisms.	2009 Jul	19422391
Improving introspection to inform free will regarding the choice by healthy individuals to use or not use cognitive enhancing drugs.	2009 Jun 16	19531231
Planning Future Strategies for Domestic and International NeuroAIDS Research, July 24-25, 2008.	2009 Sep	19455426
Sequestered evidence and the distortion of clinical practice guidelines.	2009 Spring	19395820
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Legal remedies for medical ghostwriting: imposing fraud liability on guest authors of ghostwritten articles.	2010 Aug	21829331
The chemical basis of pharmacology.	2010 Dec 7	21058655
Of sophists and spin-doctors: industry-sponsored ghostwriting and the crisis of academic medicine.	2010 Jan	21327175
Desvenlafaxine in major depressive disorder: an evidence-based review of its place in therapy.	2010 Jun 15	20694066
Negotiating the boundary between medicine and consumer culture: online marketing of nutrigenetic tests.	2010 Mar	20022680
Could chiropractors screen for adverse drug events in the community? Survey of US chiropractors.	2010 Nov 17	21083911
The haunting of medical journals: how ghostwriting sold "HRT".	2010 Sep 7	20838656
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

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 `Fri Dec 15 15:16:05 GMT 2023` Edited by `admin` on `Fri Dec 15 15:16:05 GMT 2023`
Record UNII	42B4PDY0AV
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ADIPHENINE HYDROCHLORIDE

Official Name

English

NSC-129224

Code

English

ADIPHENINE HYDROCHLORIDE [MI]

Common Name

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