MedKoo Cat#: 555588 | Name: Apomorphine HCl hydrate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Apomorphine, also known as APL-130277 and TAK-251, is a dopamine D2 agonist used for the treatment of Parkinson's disease. Apomorphine also promotes intraneuronal amyloid-β (Aβ) degradation and improves memory function in an Alzheimer's disease model. Protein levels of two types of serine-phosphorylated insulin receptor substrate-1 (IRS-1), pS616 and pS636/639, significantly decreased following Apomorphine treatment in the 13-month-old 3xTg-AD mice brain, suggesting improved brain insulin resistance.

Chemical Structure

Apomorphine HCl hydrate
Apomorphine HCl hydrate
CAS#41372-20-7 (HCl hydrate)

Theoretical Analysis

MedKoo Cat#: 555588

Name: Apomorphine HCl hydrate

CAS#: 41372-20-7 (HCl hydrate)

Chemical Formula: C34H38Cl2N2O5

Exact Mass: 267.1259

Molecular Weight: 625.59

Elemental Analysis: C, 65.28; H, 6.12; Cl, 11.33; N, 4.48; O, 12.79

Price and Availability

Related CAS #
Synonym
Apomorphine Hydrochloride, Apomorphine HCl, APL-130277, APL130277, APL 130277, KW-6500, KW 6500, KW6500, ND-0701, ND 0701, ND0701, TAK-251, TAK251, TAK 251, VR-004, VR 004, VR004, VR-040, VR 040, VR040; ; Apomorphine HCl hydrate; Apmorphine hydrochloride hemihydrate; Apokyn;
IUPAC/Chemical Name
(R)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol hydrochloride hemihydrate
InChi Key
CXWQXGNFZLHLHQ-DPFCLETOSA-N
InChi Code
InChI=1S/2C17H17NO2.2ClH.H2O/c2*1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12;;;/h2*2-6,13,19-20H,7-9H2,1H3;2*1H;1H2/t2*13-;;;/m11.../s1
SMILES Code
OC1=CC=C2C(C3=C4C(CCN(C)[C@]4([H])C2)=CC=C3)=C1O.[H]Cl.[H]O[H].OC5=CC=C6C(C7=C8C(CCN(C)[C@]8([H])C6)=CC=C7)=C5O.[H]Cl
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 625.59 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
1: Bredewold R, Nascimento NF, Ro GS, Cieslewski SE, Reppucci CJ, Veenema AH. Involvement of dopamine, but not norepinephrine, in the sex-specific regulation of juvenile socially rewarding behavior by vasopressin. Neuropsychopharmacology. 2018 May 22. doi: 10.1038/s41386-018-0100-2. [Epub ahead of print] PubMed PMID: 29875448. 2: Tong H, Zhang X, Meng X, Lu L, Mai D, Qu S. Simvastatin Inhibits Activation of NADPH Oxidase/p38 MAPK Pathway and Enhances Expression of Antioxidant Protein in Parkinson Disease Models. Front Mol Neurosci. 2018 May 22;11:165. doi: 10.3389/fnmol.2018.00165. eCollection 2018. PubMed PMID: 29872377; PubMed Central PMCID: PMC5972184. 3: Huang F, Zhang L, Wang Q, Yang Y, Li Q, Wu Y, Chen J, Qu J, Zhou X. Dopamine D1 Receptors Contribute Critically to the Apomorphine-Induced Inhibition of Form-Deprivation Myopia in Mice. Invest Ophthalmol Vis Sci. 2018 May 1;59(6):2623-2634. doi: 10.1167/iovs.17-22578. PubMed PMID: 29847669. 4: Nakashima A, Yamauchi A, Matsumoto J, Dohgu S, Takata F, Koga M, Fukae J, Tsuboi Y, Kataoka Y. Feeding-produced subchronic high plasma levels of uric acid improve behavioral dysfunction in 6-hydroxydopamine-induced mouse model of Parkinson's disease. Behav Pharmacol. 2018 May 25. doi: 10.1097/FBP.0000000000000413. [Epub ahead of print] PubMed PMID: 29847340. 5: Nakhaeifard M, Haji Ghasem Kashani M, Goudarzi I, Rezaei A. Conditioned Medium Protects Dopaminergic Neurons in Parkinsonian Rats. Cell J. 2018 Oct;20(3):348-354. doi: 10.22074/cellj.2018.5343. Epub 2018 May 15. PubMed PMID: 29845788. 6: Keshavarzian E, Ghasemzadeh Z, Rezayof A. The basolateral amygdala dopaminergic system contributes to the improving effect of nicotine on stress-induced memory impairment in rats. Prog Neuropsychopharmacol Biol Psychiatry. 2018 May 18;86:30-35. doi: 10.1016/j.pnpbp.2018.05.008. [Epub ahead of print] PubMed PMID: 29775630. 7: Alzoubi KH, Mokhemer E, Abuirmeileh AN. Beneficial effect of etazolate on depression-like behavior and, learning, and memory impairment in a model of Parkinson's disease. Behav Brain Res. 2018 Sep 17;350:109-115. doi: 10.1016/j.bbr.2018.05.004. Epub 2018 May 11. PubMed PMID: 29758248. 8: Nabavi SM, Uriarte E, Rastrelli L, Sobarzo-Sanchez E. Aporphines and Alzheimer's disease: Towards a Medical Approach Facing the Future. Curr Med Chem. 2018 May 13. doi: 10.2174/0929867325666180514102933. [Epub ahead of print] PubMed PMID: 29756568. 9: Auffret M, Drapier S, Vérin M. Correction to: The Many Faces of Apomorphine: Lessons from the Past and Challenges for the Future. Drugs R D. 2018 May 8. doi: 10.1007/s40268-018-0233-0. [Epub ahead of print] PubMed PMID: 29737467. 10: Wang B, Su CJ, Liu TT, Zhou Y, Feng Y, Huang Y, Liu X, Wang ZH, Chen LH, Luo WF, Liu T. The Neuroprotection of Low-Dose Morphine in Cellular and Animal Models of Parkinson's Disease Through Ameliorating Endoplasmic Reticulum (ER) Stress and Activating Autophagy. Front Mol Neurosci. 2018 Apr 20;11:120. doi: 10.3389/fnmol.2018.00120. eCollection 2018. PubMed PMID: 29731707; PubMed Central PMCID: PMC5920031. 11: Sarukhani M, Haghdoost-Yazdi H, Sarbazi Golezari A, Babayan-Tazehkand A, Dargahi T, Rastgoo N. Evaluation of the antiparkinsonism and neuroprotective effects of hydrogen sulfide in acute 6-hydroxydopamine-induced animal model of Parkinson's disease: behavioral, histological and biochemical studies. Neurol Res. 2018 May 4:1-9. doi: 10.1080/01616412.2017.1390903. [Epub ahead of print] PubMed PMID: 29726751. 12: Tamano H, Nishio R, Morioka H, Takeda A. Extracellular Zn(2+) Influx into Nigral Dopaminergic Neurons Plays a Key Role for Pathogenesis of 6-Hydroxydopamine-Induced Parkinson's Disease in Rats. Mol Neurobiol. 2018 Apr 29. doi: 10.1007/s12035-018-1075-z. [Epub ahead of print] PubMed PMID: 29705946. 13: Béreau M, Tomkova E, Zacharia A, Bouthour W, Fleury V, Bally JF, Horvath J, Momjian S, Lüscher C, Burkhard P, Krack P. [Advanced Parkinson's disease : indication for complex treatments]. Rev Med Suisse. 2018 Apr 25;14(604):875-878. French. PubMed PMID: 29701432. 14: Bownik A, Sokołowska N, Ślaska B. Effects of apomorphine, a dopamine agonist, on Daphnia magna: Imaging of swimming track density as a novel tool in the assessment of swimming activity. Sci Total Environ. 2018 Sep 1;635:249-258. doi: 10.1016/j.scitotenv.2018.04.157. Epub 2018 Apr 24. PubMed PMID: 29669297. 15: Yu YW, Hsueh SC, Lai JH, Chen YH, Kang SJ, Chen KY, Hsieh TH, Hoffer BJ, Li Y, Greig NH, Chiang YH. Glucose-Dependent Insulinotropic Polypeptide Mitigates 6-OHDA-Induced Behavioral Impairments in Parkinsonian Rats. Int J Mol Sci. 2018 Apr 11;19(4). pii: E1153. doi: 10.3390/ijms19041153. PubMed PMID: 29641447. 16: Ramot Y, Nyska A, Adar L, Durlach C, Fishelovitch D, Sacco G, Manno RA, Oren S, Perlstein I, Yacobi-Zeevi O. ND0701, A Novel Formulation of Apomorphine for Subcutaneous Infusion, in Comparison to a Commercial Apomorphine Formulation: 28-Day Pharmacokinetic Study in Minipigs and a Phase I Study in Healthy Volunteers to Assess the Safety, Tolerability, Pharmacokinetics and Relative Bioavailability. CNS Drugs. 2018 May;32(5):443-454. doi: 10.1007/s40263-018-0512-x. PubMed PMID: 29637529. 17: Haddad M, Pud D, Treister R, Suzan E, Eisenberg E. The effects of a dopamine agonist (apomorphine) on experimental and spontaneous pain in patients with chronic radicular pain: A randomized, double-blind, placebo-controlled, cross-over study. PLoS One. 2018 Apr 5;13(4):e0195287. doi: 10.1371/journal.pone.0195287. eCollection 2018. PubMed PMID: 29621293; PubMed Central PMCID: PMC5886417. 18: Ikram H, Zakir R, Haleem DJ. Effects of single administration of apomorphine on memory and monoamine metabolism: A dose related study. Pak J Pharm Sci. 2018 Mar;31(2):439-445. PubMed PMID: 29618432. 19: Sarukhani MR, Haghdoost-Yazdi H, Khandan-Chelarci G. Changes in the Serum Urate Level Can Predict the Development of Parkinsonism in the 6-Hydroxydopamine Animal Model. Neurochem Res. 2018 May;43(5):1086-1095. doi: 10.1007/s11064-018-2522-y. Epub 2018 Apr 3. PubMed PMID: 29616443. 20: Mack JM, Moura TM, Lanznaster D, Bobinski F, Massari CM, Sampaio TB, Schmitz AE, Souza LF, Walz R, Tasca CI, Poli A, Doty RL, Dafre AL, Prediger RD. Intranasal administration of sodium dimethyldithiocarbamate induces motor deficits and dopaminergic dysfunction in mice. Neurotoxicology. 2018 May;66:107-120. doi: 10.1016/j.neuro.2018.03.011. Epub 2018 Mar 29. PubMed PMID: 29605442.