ADIPHENINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H25NO2
Molecular Weight	311.418
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=JGOAIQNSOGZNBX-UHFFFAOYSA-N

InChI=1S/C20H25NO2/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

HIDE SMILES / InChI

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https://www.ncbi.nlm.nih.gov/pubmed/14353164 https://www.ncbi.nlm.nih.gov/pubmed/13977229	Primary		Withdrawn	Trasentine Approved Use Adiphenine is indicated for the treatment of spasms of smooth muscles of the digestive tract, bile ducts, bronchi.
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391	Primary		Withdrawn	Trasentine Approved Use Unknown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
Paxil and self-scratching.	2001 Jan	11195562
Serotonin and depression: a disconnect between the advertisements and the scientific literature.	2005 Dec	16268734
Paroxetine versus placebo and other agents for depressive disorders: a systematic review and meta-analysis.	2007 Dec	18162015
Prevalence and predictors of antidepressant use in a cohort of pregnant women.	2007 Sep	17565615
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

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)).

Name

Type

Language

ADIPHENINE

Official Name

English

2-(DIETHYLAMINO)ETHYL DIPHENYLACETATE

Systematic Name

English

ADIPHENINE [MART.]

Common Name

English

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

Common Name

English

ADIPHENINE [MI]

Common Name

English

Adiphenine [WHO-DD]

Common Name

English

ADIPHENINE [HSDB]

Common Name

English

adiphenine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29698