D054

Sigma-Aldrich

R(+)-SCH-23390 hydrochloride

≥98% (HPLC), solid

Synonym(s):
R(+)-7-Chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
Empirical Formula (Hill Notation):
C17H18ClNO · HCl
CAS Number:
Molecular Weight:
324.24
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

optical activity

[α]/D +32.1°, c = 1 in DMF(lit.)

storage condition

protect from light

color

white

solubility

H2O: >5 mg/mL

SMILES string

Cl[H].CN1CCc2cc(Cl)c(O)cc2[C@H](C1)c3ccccc3

InChI

1S/C17H18ClNO.ClH/c1-19-8-7-13-9-16(18)17(20)10-14(13)15(11-19)12-5-3-2-4-6-12;/h2-6,9-10,15,20H,7-8,11H2,1H3;1H/t15-;/m1./s1

InChI key

OYCAEWMSOPMASE-XFULWGLBSA-N

Gene Information

human ... DRD1(1812)

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Application

R(+)-SCH-23390 hydrochloride has been used:
  • for intraperitoneal injection into experimental rats to study the role of D1 receptor in sensitization
  • as a D1 receptor-selective antagonist for intracranial drug infusions
  • as an antagonist of D1 receptor to study its effect on learning ability in fish

Packaging

5, 10, 25, 100 mg in glass bottle

Biochem/physiol Actions

R(+)-SCH-23390 hydrochloride is a selective D1 dopamine receptor antagonist. It has greater binding capacity towards 5-hydroxytryptamine 2 (5-HT2) and 5-HT1C serotonin receptor subtypes in in vitro. R(+)-SCH-23390 has a half-life of about 25 minutes after administration. It is known to possess anti-stereotypic effect and cataleptogenic effect. It also has inhibitory effect on motor activity.

Features and Benefits

This compound is featured on the Dopamine Receptors and Potassium Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

Sold with the permission of Schering-Plough.
LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  6. How do I dissolve Product D054, R(+)-SCH-23390 hydrochloride?

    The D054 is tested for solublity in water at > 5 mg/mL. The product is also reported to be soluble in DMSO at 3mg/mL, and in ethanol at 2 mg/mL.

  7. What is the solution stability of Product D054, R(+)-SCH-23390 hydrochloride?

    Solutions may be stored for approximately 24 hours at 2-8 °C, protected from exposure to light.

  8. Is Product D054, R(+)-SCH-23390 hydrochloride, light sensitive?

    Yes, D054 is light sensitive. The powder form of the product, as well as solutions of the product, need to be protected from light.

  9. What is the melting point of Product D054, R(+)-SCH-23390 hydrochloride?

    The melting point is 247-248°C.

  10. Is Product D054, R(+)-SCH-23390 hydrochloride, only selective for the D1 dopamine receptor antagonist?

    The D054 is a selective D1 dopamine receptor antagonist, but is also selective to the D5. 

Rewarding properties of methylphenidate: sensitization by prior exposure to the drug and effects of dopamine D1-and D2-receptor antagonists
Meririnne E, et al.
Journal of Pharmacology and Experimental Therapeutics, 298(2), 539-550 (2001)
A Sidhu et al.
European journal of pharmacology, 128(3), 213-220 (1986-09-09)
[125I]SCH 23982, [125I]8-iodo-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine-7-ol, binds reversibly and with high affinity (Kd = 0.7 +/- 0.05 nM) to specific binding sites (maximum binding = 108 +/- 3.5 fmol/mg) in the caudate nucleus of the rat brain. The caudate binding site displays pharmacological...
SCH 23390: the first selective dopamine D1-like receptor antagonist
Bourne James A
Cns Drug Reviews, 7(4), 399-414 (2001)
K M O'Boyle et al.
Journal of neurochemistry, 48(4), 1039-1042 (1987-04-01)
A series of 1-phenyl-1H-3-benzazepine analogues were assessed for enantiomeric and structure-affinity relationships at human putamen D-1 dopamine receptors labelled with [3H]SCH 23390. Substitution at the 7-position of both 3-H and 3-methyl benzazepine molecules critically affected affinity for these receptors over...
L C Iorio et al.
The Journal of pharmacology and experimental therapeutics, 226(2), 462-468 (1983-08-01)
SCH 23390 [R-(+)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepine-7-ol) possesses pharmacologic effects similar to standard antipsychotics, including selective supression of conditioned avoidance responding in rats and squirrel monkeys, blockade of apomorphine-induced stereotypy in rats and blockade of methamphetamine-induced lethality in aggregated mice. At effective doses in...

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