Purmorphamine | CAS#483367-10-8 | Hedgehog agonist

MedKoo Cat#: 406133 | Name: Purmorphamine

Description:

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

Purmorphamine is a Hedgehog agonist, which activates the Hedgehog pathway by targeting Smoothened. Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway. Purmorphamine increases DARPP-32 differentiation in human striatal neural stem cells through the Hedgehog pathway. Purmorphamine enhances osteogenic activity of human osteoblasts derived from bone marrow mesenchymal cells. Hedgehog (Hh) signaling is an important regulator of embryonic patterning, tissue regeneration, stem cell renewal and cancer growth.

Chemical Structure

Purmorphamine

CAS#483367-10-8

Theoretical Analysis

MedKoo Cat#: 406133

Name: Purmorphamine

CAS#: 483367-10-8

Chemical Formula: C31H32N6O2

Exact Mass: 520.2587

Molecular Weight: 520.62

Elemental Analysis: C, 71.52; H, 6.20; N, 16.14; O, 6.15

Price and Availability

Size	Price	Availability
5mg	USD 110.00	Ready to ship
10mg	USD 180.00	Ready to ship
25mg	USD 385.00	Ready to ship
50mg	USD 650.00	Ready to ship
100mg	USD 1,050.00	Ready to ship
200mg	USD 1,850.00	Ready to ship

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Related CAS #

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Synonym

Purmorphamine

IUPAC/Chemical Name

9-cyclohexyl-N-(4-morpholinophenyl)-2-(naphthalen-1-yloxy)-9H-purin-6-amine

InChi Key

FYBHCRQFSFYWPY-UHFFFAOYSA-N

InChi Code

InChI=1S/C31H32N6O2/c1-2-9-25(10-3-1)37-21-32-28-29(33-23-13-15-24(16-14-23)36-17-19-38-20-18-36)34-31(35-30(28)37)39-27-12-6-8-22-7-4-5-11-26(22)27/h4-8,11-16,21,25H,1-3,9-10,17-20H2,(H,33,34,35)

SMILES Code

N1(C2CCCCC2)C=NC3=C(NC4=CC=C(N5CCOCC5)C=C4)N=C(OC6=C7C=CC=CC7=CC=C6)N=C13

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, not soluble in water.

Shelf Life

>5 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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A20T11K14

QC Data

View QC data: current batch, Lot#A20T11K14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Purmorphamine (Shh Signaling Antagonist VI) is a smoothened/Smo receptor agonist with an EC50 of 1 μM.

In vitro activity:

Purmorphamine stimulates Müller glial cell proliferation by upregulating cyclin D1 and cyclin D3 expression. Purmorphamine induces dedifferentiation of these cells, leading to the expression of progenitor-specific markers and their subsequent differentiation into rod-like photoreceptors. These results indicate that purmorphamine has the potential to enhance the endogenous neurogenic capacity of Müller glial cells, making it a promising candidate for retinal regeneration therapies. Reference: Mol Med Rep. 2017 Dec; 16(6): 7993–8002. https://pubmed.ncbi.nlm.nih.gov/28983586/

In vivo activity:

Purmorphamine demonstrated neuroprotective activity in neonatal mice experiencing hypoxic-ischemic (HI) brain injury. PUR mitigated acute brain injury by reducing the Bax/Bcl-2 ratio and inhibiting caspase-3 activation. PUR reduced tissue loss and improved neurobehavioral outcomes up to 28 days post-HI injury. It enhanced the expression of synaptic markers and counters synaptic loss, potentially enhancing neural connectivity. Reference: Front Pharmacol. 2020; 11: 204. https://pubmed.ncbi.nlm.nih.gov/32194421/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	19.20

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 520.62 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.

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:

1. Gu D, Wang S, Zhang S, Zhang P, Zhou G. Directed transdifferentiation of Müller glial cells to photoreceptors using the sonic hedgehog signaling pathway agonist purmorphamine. Mol Med Rep. 2017 Dec;16(6):7993-8002. doi: 10.3892/mmr.2017.7652. Epub 2017 Sep 28. PMID: 28983586; PMCID: PMC5779882. 2. Bahrami N, Malekolkottab F, Ebrahimi-Barough S, Alizadeh Tabari Z, Hamisi J, Kamyab A, Mohamadnia A, Ai A, Bayat F, Bahrami N, Ai J. The effect of purmorphamine on differentiation of endometrial stem cells into osteoblast-like cells on collagen/hydroxyapatite scaffolds. Artif Cells Nanomed Biotechnol. 2017 Nov;45(7):1343-1349. doi: 10.1080/21691401.2016.1236804. Epub 2016 Sep 30. PMID: 27686538. 3. Rahi S, Gupta R, Sharma A, Mehan S. Smo-Shh signaling activator purmorphamine ameliorates neurobehavioral, molecular, and morphological alterations in an intracerebroventricular propionic acid-induced experimental model of autism. Hum Exp Toxicol. 2021 Apr 28:9603271211013456. doi: 10.1177/09603271211013456. Epub ahead of print. PMID: 33906504. 4. Liu D, Bai X, Ma W, Xin D, Chu X, Yuan H, Qiu J, Ke H, Yin S, Chen W, Wang Z. Purmorphamine Attenuates Neuro-Inflammation and Synaptic Impairments After Hypoxic-Ischemic Injury in Neonatal Mice via Shh Signaling. Front Pharmacol. 2020 Mar 4;11:204. doi: 10.3389/fphar.2020.00204. PMID: 32194421; PMCID: PMC7064623.

In vitro protocol:

In vivo protocol:

1. Rahi S, Gupta R, Sharma A, Mehan S. Smo-Shh signaling activator purmorphamine ameliorates neurobehavioral, molecular, and morphological alterations in an intracerebroventricular propionic acid-induced experimental model of autism. Hum Exp Toxicol. 2021 Apr 28:9603271211013456. doi: 10.1177/09603271211013456. Epub ahead of print. PMID: 33906504. 2. Liu D, Bai X, Ma W, Xin D, Chu X, Yuan H, Qiu J, Ke H, Yin S, Chen W, Wang Z. Purmorphamine Attenuates Neuro-Inflammation and Synaptic Impairments After Hypoxic-Ischemic Injury in Neonatal Mice via Shh Signaling. Front Pharmacol. 2020 Mar 4;11:204. doi: 10.3389/fphar.2020.00204. PMID: 32194421; PMCID: PMC7064623.

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PMID: 38673725; PMCID: PMC11049943. 5: Li Y, Xu J, Jiang C, Chen Z, Chen Y, Ying M, Wang A, Ma C, Wang C, Guo Y, Liu C. [Rho kinase inhibitor Y27632 promotes survival of human induced pluripotent stem cells during differentiation into functional midbrain dopaminergic progenitor cells in vitro]. Nan Fang Yi Ke Da Xue Xue Bao. 2024 Feb 20;44(2):236-243. Chinese. doi: 10.12122/j.issn.1673-4254.2024.02.05. PMID: 38501408; PMCID: PMC10954535. 6: Zou Y, Wu S, Hu Q, Zhou H, Ge Y, Ju Z, Luo S. Sonic hedgehog restrains the ubiquitin-dependent degradation of SP1 to inhibit neuronal/glial senescence associated phenotypes in chemotherapy-induced peripheral neuropathy via the TRIM25-CXCL13 axis. J Adv Res. 2024 Mar 12:S2090-1232(24)00106-1. doi: 10.1016/j.jare.2024.03.006. Epub ahead of print. PMID: 38479571. 7: Peredo AP, Tsinman TK, Bonnevie ED, Jiang X, Smith HE, Gullbrand SE, Dyment NA, Mauck RL. Developmental morphogens direct human induced pluripotent stem cells toward an annulus fibrosus-like cell phenotype. JOR Spine. 2024 Jan 25;7(1):e1313. doi: 10.1002/jsp2.1313. PMID: 38283179; PMCID: PMC10810760. 8: Prajapati A, Mehan S, Khan Z, Chhabra S, Das Gupta G. Purmorphamine, a Smo- Shh/Gli Activator, Promotes Sonic Hedgehog-Mediated Neurogenesis and Restores Behavioural and Neurochemical Deficits in Experimental Model of Multiple Sclerosis. Neurochem Res. 2024 Jun;49(6):1556-1576. doi: 10.1007/s11064-023-04082-9. Epub 2023 Dec 30. PMID: 38160216. 9: Quintero-Espinosa DA, Velez-Pardo C, Jimenez-Del-Rio M. High Yield of Functional Dopamine-like Neurons Obtained in NeuroForsk 2.0 Medium to Study Acute and Chronic Rotenone Effects on Oxidative Stress, Autophagy, and Apoptosis. Int J Mol Sci. 2023 Oct 30;24(21):15744. doi: 10.3390/ijms242115744. PMID: 37958728; PMCID: PMC10647258. 10: Wolf MTF, Bonsib SM, Larsen CP, Hildebrandt F. Nephronophthisis: a pathological and genetic perspective. Pediatr Nephrol. 2024 Jul;39(7):1977-2000. doi: 10.1007/s00467-023-06174-8. Epub 2023 Nov 6. PMID: 37930417. 11: Martinez-Heredia V, Blackwell D, Sebastian S, Pearson T, Mok GF, Mincarelli L, Utting C, Folkes L, Poeschl E, Macaulay I, Mayer U, Münsterberg A. Absence of the primary cilia formation gene Talpid3 impairs muscle stem cell function. Commun Biol. 2023 Nov 4;6(1):1121. doi: 10.1038/s42003-023-05503-9. PMID: 37925530; PMCID: PMC10625638. 12: Yuan F, Bai K, Hou Y, Zou X, Sun J. Small Molecule Cocktails Promote Fibroblast-to-Leydig-like Cell Conversion for Hypogonadism Therapy. Pharmaceutics. 2023 Oct 13;15(10):2456. doi: 10.3390/pharmaceutics15102456. PMID: 37896216; PMCID: PMC10610100. 13: Zhang Y, Xie CL, Wang Y, He XW, Xie MM, Li Y, Zhang K, Zou ZB, Yang LH, Xu R, Yang XW. Penidihydrocitrinins A-C: New Polyketides from the Deep-Sea-Derived Penicillium citrinum W17 and Their Anti-Inflammatory and Anti- Osteoporotic Bioactivities. Mar Drugs. 2023 Oct 14;21(10):538. doi: 10.3390/md21100538. PMID: 37888473; PMCID: PMC10608093. 14: Souza PG, Adolpho LF, Lopes HB, Weffort D, Souza ATP, Oliveira FS, Rosa AL, Beloti MM. Effects of Modulation of the Hedgehog and Notch Signaling Pathways on Osteoblast Differentiation Induced by Titanium with Nanotopography. J Funct Biomater. 2023 Jan 30;14(2):79. doi: 10.3390/jfb14020079. PMID: 36826878; PMCID: PMC9968096. 15: Li L, Dong Q, Wang Y, Feng Q, Zhou P, Ou X, Meng Q, He T, Luo J. [Retracted] Hedgehog signaling is involved in the BMP9‑induced osteogenic differentiation of mesenchymal stem cells. Int J Mol Med. 2023 Apr;51(4):30. doi: 10.3892/ijmm.2023.5233. Epub 2023 Feb 24. PMID: 36825560; PMCID: PMC10049012. 16: Khara LS, Ali DW. The endocannabinoid system's involvement in motor development relies on cannabinoid receptors, TRP channels, and Sonic Hedgehog signaling. Physiol Rep. 2023 Jan;11(1):e15565. doi: 10.14814/phy2.15565. PMID: 36636759; PMCID: PMC9837476. 17: Xu Y, Sun H. Involvement of hedgehog signaling in all-trans retinoic acid- mediated suppression of colon cancer. Am J Transl Res. 2022 Sep 15;14(9):6536-6549. PMID: 36247302; PMCID: PMC9556466. 18: Jiang J, Liu Z, Zhou X, Peng F, Wang Z, Li F, Li M. Resveratrol Induces Apoptosis, Suppresses Migration, and Invasion of Cervical Cancer Cells by Inhibiting the Hedgehog Signaling Pathway. Biomed Res Int. 2022 Oct 7;2022:8453011. doi: 10.1155/2022/8453011. PMID: 36246980; PMCID: PMC9568329. 19: Singh K, Nawabjan SA, Zhang L, El-Nezami H, Annapureddy RR, Chow BK. Discovery of small-molecule modulators of the secretin receptor: Purmorphamine as novel anti-hypertensive agent. Eur J Med Chem. 2022 Nov 15;242:114642. doi: 10.1016/j.ejmech.2022.114642. Epub 2022 Aug 5. PMID: 35987021. 20: Hua T, Liu C, Kiran S, Gray K, Jung S, Meckes DG Jr, Li Y, Sang QA. Phenotypic, metabolic, and biogenesis properties of human stem cell-derived cerebellar spheroids. Sci Rep. 2022 Jul 27;12(1):12880. doi: 10.1038/s41598-022-16970-1. PMID: 35896708; PMCID: PMC9329474.