Odapipam

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MedKoo CAT#: 414439

CAS#: 131796-63-9

Description: Odapipam is a benzazepine with high affinity and selectivity for D1-dopamine receptors. Labeled with C-11, it has been used as a PET radiotracer to visualize D1 receptors both in striatal and extrastriatal areas, such as the prefrontal cortex. Odapipam inhibits dopamine D1 receptor binding in vitro with low nanomolar to picomolar dissociation constants. The affinity of [11C]NNC 756 for D1 receptors is 0.18 nM. Odapipam was tested in phase I of clinical trials for the treatment of psychotic disorders, but failed.


Chemical Structure

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Odapipam
CAS# 131796-63-9

Theoretical Analysis

MedKoo Cat#: 414439
Name: Odapipam
CAS#: 131796-63-9
Chemical Formula: C19H20ClNO2
Exact Mass: 329.12
Molecular Weight: 329.820
Elemental Analysis: C, 69.19; H, 6.11; Cl, 10.75; N, 4.25; O, 9.70

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Odapipam; NNC756; NNC-756; NNC 756

IUPAC/Chemical Name: ( )-(S)-8-Chloro-5-(2,3-dihydro-7-benzofuranyl)-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepin-7-ol

InChi Key: SKMVRXPBCSTNKE-MRXNPFEDSA-N

InChi Code: InChI=1S/C19H20ClNO2/c1-21-7-5-13-9-17(20)18(22)10-15(13)16(11-21)14-4-2-3-12-6-8-23-19(12)14/h2-4,9-10,16,22H,5-8,11H2,1H3/t16-/m1/s1

SMILES Code: OC1=C(Cl)C=C2CCN(C)C[C@H](C3=C(OCC4)C4=CC=C3)C2=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 329.82 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Andersen JV, Hansen KT. Normal-phase liquid chromatography-particle-beam mass spectrometry in drug metabolism studies of the dopamine receptor antagonist Odapipam and the muscarine M1 receptor agonist Xanomeline. Xenobiotica. 1997 Sep;27(9):901-12. doi: 10.1080/004982597240073. PMID: 9381731.

2: Hansen KT, Stentoft K. Characterization of benzazepine UDP-glucuronosyl- transferases in laboratory animals and man. Xenobiotica. 1995 Jun;25(6):611-22. doi: 10.3109/00498259509061879. PMID: 7483661.

3: Hagelberg N, Forssell H, Aalto S, Rinne JO, Scheinin H, Taiminen T, Någren K, Eskola O, Jääskeläinen SK. Altered dopamine D2 receptor binding in atypical facial pain. Pain. 2003 Nov;106(1-2):43-8. doi: 10.1016/s0304-3959(03)00275-6. PMID: 14581109.

4: Hagelberg N, Forssell H, Rinne JO, Scheinin H, Taiminen T, Aalto S, Luutonen S, Någren K, Jääskeläinen S. Striatal dopamine D1 and D2 receptors in burning mouth syndrome. Pain. 2003 Jan;101(1-2):149-54. doi: 10.1016/s0304-3959(02)00323-8. PMID: 12507709.

5: Pascoe PJ, Taylor PM. Effects of dopamine antagonists on alfentanil-induced locomotor activity in horses. Vet Anaesth Analg. 2003 Jul;30(3):165-71. doi: 10.1046/j.1467-2995.2003.00134.x. PMID: 14498848.

6: Andersen PH, Grønvald FC, Hohlweg R, Hansen LB, Guddal E, Braestrup C, Nielsen EB. NNC-112, NNC-687 and NNC-756, new selective and highly potent dopamine D1 receptor antagonists. Eur J Pharmacol. 1992 Aug 14;219(1):45-52. doi: 10.1016/0014-2999(92)90578-r. PMID: 1397049.

7: Abi-Dargham A, Simpson N, Kegeles L, Parsey R, Hwang DR, Anjilvel S, Zea- Ponce Y, Lombardo I, Van Heertum R, Mann JJ, Foged C, Halldin C, Laruelle M. PET studies of binding competition between endogenous dopamine and the D1 radiotracer [11C]NNC 756. Synapse. 1999 May;32(2):93-109. doi: 10.1002/(SICI)1098-2396(199905)32:2<93::AID-SYN3>3.0.CO;2-C. PMID: 10231129.

8: Laihinen AO, Rinne JO, Ruottinen HM, Någren KA, Lehikoinen PK, Oikonen VJ, Ruotsalainen UH, Rinne UK. PET studies on dopamine D1 receptors in the human brain with carbon-11-SCH 39166 and carbon-11-NNC 756. J Nucl Med. 1994 Dec;35(12):1916-20. PMID: 7989969.

9: Peacock L, Hansen L, Mørkeberg F, Gerlach J. Chronic dopamine D1, dopamine D2 and combined dopamine D1 and D2 antagonist treatment in Cebus apella monkeys: antiamphetamine effects and extrapyramidal side effects. Neuropsychopharmacology. 1999 Jan;20(1):35-43. doi: 10.1016/S0893-133X(98)00049-9. PMID: 9885783.

10: Hansen KT, Thomsen KF, Bundgaard H. Glucuronidation of the dopamine D-1 receptor antagonists NNC 0756 and NNC 0772 in liver microsomes. Drug Metab Dispos. 1992 Mar-Apr;20(2):172-8. PMID: 1352206.