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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=CC(OC)=C(OC)C=C23)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
Vesicular monoamine transporter 2 and the acute and long-term response to 3,4-(±)-methylenedioxymethamphetamine.
2015-01
Neuropeptide Y differentiates between exocytotic and nonexocytotic noradrenaline release in guinea-pig heart.
1989-11
Pharmacological profile of moclobemide, a short-acting and reversible inhibitor of monoamine oxidase type A.
1989-01
[Electrophysiological study of tianeptine, a new enhancer of serotonin uptake with antidepressant activity].
1988-08
Mechanisms of effects of d-fenfluramine on brain serotonin metabolism in rats: uptake inhibition versus release.
1988-07
Inhibition of basement membrane biosynthesis prevents angiogenesis.
1988-02
Brain norepinephrine and convulsions in the genetically epilepsy-prone rat: sex-dependent responses to Ro 4-1284 treatment.
1988
Rate of basement membrane biosynthesis as an index to angiogenesis.
1988
The mechanism of the 3H-noradrenaline releasing effect of various substrates of uptake1: role of monoamine oxidase and of vesicularly stored 3H-noradrenaline.
1987-12
Sleep abnormalities with REM disorder in experimental Creutzfeldt-Jakob disease in cats: a new pathological feature.
1987-05-19
Differences between the neuronal handling of 3H-7- and 3H-7,8-(-)noradrenaline: implications for the release of the labelled neurotransmitter by nerve stimulation.
1987-02
Errors introduced by a tritium label in position 8 of catecholamines.
1986-01
Selective noradrenaline depletion markedly alters stress responses in rats.
1985-08-05
Effects of amfonelic acid, alpha-methyltyrosine, Ro 4-1284 and haloperidol pretreatment on the depletion of striatal dopamine by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in mice.
1985-04
Inhibition of types A and B monoamine oxidase by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.
1985-03
Alpha 2-adrenoceptor antagonism and other pharmacological antagonist properties of some substituted benzoquinolizines and yohimbine in vitro.
1984-10
The outward transport of axoplasmic noradrenaline induced by a rise of the sodium concentration in the adrenergic nerve endings of the rat vas deferens.
1984-09
Studies of the alpha 2-adrenoceptor affinity and the alpha 2- to alpha 1-adrenoceptor selectivity of some substituted benzoquinolizines using receptor-binding techniques.
1984-05-01
An investigation into the selectivity of a novel series of benzoquinolizines for alpha 2-adrenoceptors in vivo.
1984-05
Comparison of the effects of beta-phenylethylamine and d-amphetamine on rat isolated atria.
1983-10
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.
1983-10
[Structure and synthesis of benzoquinolizidine alkaloids isolated from Alangium lamarckii].
1983-03
Drug-induced release of biogenic amines from synaptosomes and blood platelets of guinea-pigs.
1982-09
An improved pharmacological procedure for depletion of noradrenaline: pharmacology and assessment of noradrenaline-associated behaviors.
1982-02-05
The role of norepinephrine in feeding behavior.
1982
Effect of Ro 4-1284 on audiogenic seizure susceptibility and intensity in epilepsy-prone rats.
1981-05-04
Liberation of catecholamines and 5-hydroxytryptamine from human blood-platelets.
1981-02
Liberation of catecholamines from blood platelets.
1981-02
Depletion of epinephrine in rat hypothalamus by Ro 4-1284: influence of pargyline and harmaline.
1980-09-01
The effect of pargyline pretreatment on the enhancement of the exocytotic release of norepinephrine during nerve stimulation which is induced by a benzoquinolizine compound with reserpine-like properties.
1980-06
In vivo monoamine oxidase inhibition by d-amphetamine.
1980-05-15
Synergism of the toxicity of physostigmine and neostigmine by lithium or by a reserpine-like agent (Ro4-1284).
1980
A comparison of cochlear microphonics and N1 in audiogenic-seizure-susceptible and control rats.
1980
Forced swimming in rats: hypothermia, immobility and the effects of imipramine.
1979-08-15
Uptake of 5-hydroxytryptamine in blood platelets and its inhibition by drugs: role of plasma membrane and granular storage.
1979-05
Metabolism and efflux of [3H]dopamine in rat neostriatum: presynaptic origin of 3,4-[3H]dihydroxyphenylacetic acid.
1979-05
Synthesis of potential antineoplastic agents XXVI: 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]2-quinolizinone derivatives.
1978-06
Enhancement of 5-hydroxytryptamine synthesis in brain by monamine-depleting drugs.
1978-02
Effects of L-dopa, GPA 1734 and other agents on basement membrane biosynthesis.
1978-02
Choline acetyltransferase and acetylcholinesterase activities in mice brain during the antagonistic action of antidepressant drugs and Ro 4--1284.
1978-01-01
Effects of Ro 4-1284 on electrically-induced spinal cord seizures and on spinal cord norepinephrine and 5-hydroxytryptamine levels.
1977-12
A benzo[a]quinolizine derivative with a neuroleptic-like action on cerebral monoamine turnover.
1977-12
Mechanisms underlying modifications in the severity of audiogenic convulsions.
1977-06-15
Possible physiological significance of the initial step in the catabolism of noradrenaline in the central nervous system of the rat.
1977-03
Effect of neuroleptics and other drugs on monoamine uptake by membranes of adrenal chromaffin granules.
1977-03
Dopamine content and synthesis in retina and n. accumbens septi: pharmacological and light-induced modifications.
1977
Interaction of psychotropic agents with central neurotransmitters as revealed by their effects on PGO waves in the cat.
1976
Release of norepinephrine and dopamine-beta-hydroxylase by nerve stimulation. V. Enhanced release associated with a granular effect of a benzoquinolizine derivative with reserpine-like properties.
1975-06
A critical study on RO-4-1284 antagonism in mice.
1975-05
Monoamine-depleting drugs.
1975
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
2H-BENZO(A)QUINOLIZIN-2-OL, 2-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-3-ISOBUTYL-9,10-DIMETHOXY-
Preferred Name English
RO-4-1284
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 Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
CAS
303-75-3
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID90952665
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
FDA UNII
H2S3M5M720
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY