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Details

Stereochemistry MIXED
Molecular Formula C21H33NO3
Molecular Weight 347.4916
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RO-4-1284

SMILES

CCC1(O)CC2N(CCC3=C2C=C(OC)C(OC)=C3)CC1CC(C)C

InChI

InChIKey=TUNMGCULOKMBNJ-UHFFFAOYSA-N
InChI=1S/C21H33NO3/c1-6-21(23)12-18-17-11-20(25-5)19(24-4)10-15(17)7-8-22(18)13-16(21)9-14(2)3/h10-11,14,16,18,23H,6-9,12-13H2,1-5H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9988119 | https://www.ncbi.nlm.nih.gov/pubmed/10773000

Ro 4-1284 is a VMAT2 inhibitor. Compond exhibits reserpine-like effect and is used as a tool compound in preclinical studies, its chronic administration lead to such symptoms as deterioration of learning, decrease in locomotion in rearing, intense hypothermia

Originator

Curator's Comment: Samples of compound for early preclinical studies dated in 1970-s were provided by Hoffman La Roche, https://www.ncbi.nlm.nih.gov/pubmed/4257629 # Hoffman La Roche

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
28.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Monoamine-depleting drugs.
1975
An evaluation of the use of intraventricularly administered [3H]5-hydroxytryptamine as a marker for endogenous brain 5-hydroxytryptamine.
1975 Jul 25
Influence of a benzoquinolizinyl derivative on serum and hepatic alkaline phosphatase activity in the dog and rat.
1975 May
A subchronic study of the toxicity of an orally administered benzoquinolizinyl derivative in the rat and dog.
1975 May
Interaction of psychotropic agents with central neurotransmitters as revealed by their effects on PGO waves in the cat.
1976
On the role of storage granules in the functional utilization of newly synthesized dopamine.
1976
Uptake and liberation of mepacrine in blood platelets.
1976
[Studies on the synthesis of isocarbostyril derivatives. (1). A novel synthesis of isocarbostyril derivatives and synthesis of protoberberine and dibenzoquinolizine derivatives (author's transl)].
1976 Feb
Drugs and PGO waves in the lateral geniculate body of the curarized cat. IV. The effects of acetylcholine, GABA and benzodiazepines on PGO wave activity.
1976 Feb
[Effects of methamphetamine and a reserpine-like drug on norepinephrine and dopamine metabolism in the rat brain].
1976 May
[Effect of lithium on the central serotonin- and adrenergic processes after its chronic administration].
1976 May-Jun
[Effects of lithium chloride administered in combination with methamphetamine or a reserpine- like drug on brain norepinephrine and dopamine metabolism in rats].
1976 Sep
Dopamine content and synthesis in retina and n. accumbens septi: pharmacological and light-induced modifications.
1977
Effects of Ro 4-1284 on electrically-induced spinal cord seizures and on spinal cord norepinephrine and 5-hydroxytryptamine levels.
1977 Dec
Mechanisms underlying modifications in the severity of audiogenic convulsions.
1977 Jun 15
Possible physiological significance of the initial step in the catabolism of noradrenaline in the central nervous system of the rat.
1977 Mar
Effect of neuroleptics and other drugs on monoamine uptake by membranes of adrenal chromaffin granules.
1977 Mar
[Ways of increasing resistance of renal transplant to thermal ischemia].
1977 Sep-Oct
Enhancement of 5-hydroxytryptamine synthesis in brain by monamine-depleting drugs.
1978 Feb
Effects of L-dopa, GPA 1734 and other agents on basement membrane biosynthesis.
1978 Feb
Choline acetyltransferase and acetylcholinesterase activities in mice brain during the antagonistic action of antidepressant drugs and Ro 4--1284.
1978 Jan-Feb
Forced swimming in rats: hypothermia, immobility and the effects of imipramine.
1979 Aug 15
A comparison of cochlear microphonics and N1 in audiogenic-seizure-susceptible and control rats.
1980
In vivo monoamine oxidase inhibition by d-amphetamine.
1980 May 15
Depletion of epinephrine in rat hypothalamus by Ro 4-1284: influence of pargyline and harmaline.
1980 Sep-Oct
An improved pharmacological procedure for depletion of noradrenaline: pharmacology and assessment of noradrenaline-associated behaviors.
1982 Feb 5
Drug-induced release of biogenic amines from synaptosomes and blood platelets of guinea-pigs.
1982 Sep
The role of norepinephrine in feeding behavior.
1982 Summer
Comparison of the effects of beta-phenylethylamine and d-amphetamine on rat isolated atria.
1983 Oct
Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s.
1983 Oct
Studies of the alpha 2-adrenoceptor affinity and the alpha 2- to alpha 1-adrenoceptor selectivity of some substituted benzoquinolizines using receptor-binding techniques.
1984 May 1
Alpha 2-adrenoceptor antagonism and other pharmacological antagonist properties of some substituted benzoquinolizines and yohimbine in vitro.
1984 Oct
The outward transport of axoplasmic noradrenaline induced by a rise of the sodium concentration in the adrenergic nerve endings of the rat vas deferens.
1984 Sep
Errors introduced by a tritium label in position 8 of catecholamines.
1986 Jan
The mechanism of the 3H-noradrenaline releasing effect of various substrates of uptake1: role of monoamine oxidase and of vesicularly stored 3H-noradrenaline.
1987 Dec
Rate of basement membrane biosynthesis as an index to angiogenesis.
1988
[Electrophysiological study of tianeptine, a new enhancer of serotonin uptake with antidepressant activity].
1988 Aug
Mechanisms of effects of d-fenfluramine on brain serotonin metabolism in rats: uptake inhibition versus release.
1988 Jul
Neuropeptide Y differentiates between exocytotic and nonexocytotic noradrenaline release in guinea-pig heart.
1989 Nov
Pharmacological inactivation of the vesicular monoamine transporter can enhance 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurodegeneration of midbrain dopaminergic neurons, but not locus coeruleus noradrenergic neurons.
2000
The control of blepharospasm by essential fatty acids.
2000
Role for dopamine in malonate-induced damage in vivo in striatum and in vitro in mesencephalic cultures.
2000 Apr
Vesicular monoamine transporter 2 and the acute and long-term response to 3,4-(±)-methylenedioxymethamphetamine.
2015 Jan
Patents

Patents

Sample Use Guides

In neurotoxicity experiments Ro4-1284 was administered to rats at doses 10 mg/kg i.p.
Route of Administration: Intraperitoneal
Inhibition of [3H]DTBZ binding (probing VMAT2) on rat synaptic vesicle membranes was measured. Ro 4-1284 inhibits binding of [3H]DTBZ with Ki of 28 nM.
Name Type Language
RO-4-1284
Common Name English
2H-BENZO(A)QUINOLIZIN-2-OL, 2-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-3-ISOBUTYL-9,10-DIMETHOXY-
Common Name English
RO 4-1284
Common Name English
2-HYDROXY-2-ETHYL-3-ISOBUTYL-9,10-DIMETHOXY-1,3,4,6,7,11B-HEXAHYDRO-2H-BENZO(A)QUINOLIZINE
Common Name English
2H-BENZO(A)QUINOLIZIN-2-OL, 2-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-3-(2-METHYLPROPYL)-
Common Name English
2-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-3-ISOBUTYL-9,10-DIMETHOXY-2H-BENZO(A)QUINOLIZIN-2-OL
Common Name English
Code System Code Type Description
PUBCHEM
9345
Created by admin on Sat Dec 16 05:27:22 GMT 2023 , Edited by admin on Sat Dec 16 05:27:22 GMT 2023
PRIMARY
CAS
303-75-3
Created by admin on Sat Dec 16 05:27:22 GMT 2023 , Edited by admin on Sat Dec 16 05:27:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID90952665
Created by admin on Sat Dec 16 05:27:22 GMT 2023 , Edited by admin on Sat Dec 16 05:27:22 GMT 2023
PRIMARY
FDA UNII
H2S3M5M720
Created by admin on Sat Dec 16 05:27:22 GMT 2023 , Edited by admin on Sat Dec 16 05:27:22 GMT 2023
PRIMARY