adamantane

tricyclo(3.3.1.13,7)decane

CAS: 281-23-2 C10 H16 MW: 136.23752000

Identification

Nameadamantane
CAS Number281-23-2
EINECS206-001-4
FDA UNIIPJY633525U
Molecular FormulaC10 H16
Molecular Weight136.23752000
MDL NumberMFCD00074719

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 205.00 °C. @ 760.00 mm Hg
Boiling Point 187.14 °C. @ 760.00 mm Hg (est)
Vapor Pressure 0.881000 mmHg @ 25.00 °C. (est)
Flash Point 120.00 °F. TCC ( 48.90 °C. ) (est)
logP (o/w) 4.240
Soluble in water, 6.033 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 > 10000 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for adamantane usage levels up tonot for fragrance use.
Recommendation for adamantane flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

blumea balsamifera

Synonyms

tricyclo(3.3.1.13,7)decane tricyclo[3.3.1.1(3,7)]decane PubMed: Pharmacological profile of natural and synthetic compounds with rigid adamantane-based scaffolds as potential agents for the treatment of neurodegenerative diseases PubMed: Leveraging a large microbial strain collection for natural product discovery PubMed: Natural products for Alzheimer's disease therapy: basic and application PubMed: Biosynthesis of thiocarboxylic acid-containing natural products PubMed: Challenges and opportunities for natural product discovery, production, and engineering in native producers versus heterologous hosts PubMed: Soluble epoxide hydrolase inhibitors with carboranes as non-natural 3-D pharmacophores PubMed: Adamantane-Substituted Acridine Donor for Blue Dual Fluorescence and Efficient Organic Light-Emitting Diodes PubMed: Strain prioritization for natural product discovery by a high-throughput real-time PCR method PubMed: Influenza viruses - antiviral therapy and resistance PubMed: Anti-adipogenicadamantane type polycyclic polyprenylated acylphloroglucinols from Hypericum subsessile PubMed: Mining and engineering natural-product biosynthetic pathways PubMed: Bioisosteric substitution of adamantane with bicyclic lipophilic groups improves water solubility of human soluble epoxide hydrolase inhibitors PubMed: Current approaches to exploit actinomycetes as a source of novel natural products PubMed: Adamantane-Based Micro- and Ultra-Microporous Frameworks for Efficient Small Gas and Toxic Organic Vapor Adsorption PubMed: Supramolecular Assembled Programmable Nanomedicine As In Situ Cancer Vaccine for Cancer Immunotherapy PubMed: Synthetic versus natural receptors: supramolecular control of chemical sensing in fish PubMed: Synthesis of platensimycin PubMed: Acid-Responsive Adamantane-Cored Amphiphilic Block Polymers as Platforms for Drug Delivery PubMed: Adipogenesis Inhibitory Activity of Hypersampsone P from Hypericum subsessile PubMed: Biodegradable Redox-Sensitive Star Polymer Nanomicelles for Enhancing Doxorubicin Delivery PubMed: Multimerization of an apoptogenic TRAIL-mimicking peptide by using adamantane-based dendrons PubMed: Organic Functionalized Graphene Oxide Behavior in Water PubMed: In-capillary derivatization with fluorescamine for the rapid determination of adamantane drugs by capillary electrophoresis with UV detection PubMed: Nano-Carriers Based on pH-Sensitive Star-Shaped Copolymers for Drug-Controlled Release PubMed: Rational Construction of Borromean Linked Crystalline Organic Polymers PubMed: Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids-New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers PubMed: Hyperacmosins E-G, three new homoadamantane-type polyprenylated acylphloroglucinols from Hypericum acmosepalum PubMed: Total Synthesis of Dapholdhamine B and Dapholdhamine B Lactone PubMed: Virtual Screening Identifies Chebulagic Acid as an Inhibitor of the M2(S31N) Viral Ion Channel and Influenza A Virus PubMed: Platensimycin and platencin: Inspirations for chemistry, biology, enzymology, and medicine PubMed: Different modes of inhibition by adamantane amine derivatives and natural polyamines of the functionally reconstituted influenza virus M2 proton channel protein PubMed: Synthesis of new pyrazolone and pyrazole-based adamantyl chalcones and antimicrobial activity PubMed: 3D-printable self-healing and mechanically reinforced hydrogels with host-guest non-covalent interactions integrated into covalently linked networks PubMed: Discovery and syntheses of "superbug challengers"-platensimycin and platencin PubMed: Biocompatible cellulose-based supramolecular nanoparticles driven by host-guest interactions for drug delivery PubMed: Total synthesis of platensimycin and related natural products PubMed: Late-Stage Functionalization of Platensimycin Leading to Multiple Analogues with Improved Antibacterial Activity in Vitro and in Vivo PubMed: Influenza A M2 Inhibitor Binding Understood through Mechanisms of Excess Proton Stabilization and Channel Dynamics PubMed: Design and synthesis of pinane oxime derivatives as novel anti-influenza agents PubMed: Synthetic peroxides as potent antimalarials. News and views PubMed: Fluorescent Metallacycle-Cored Amphiphilic Nanoparticles Formed by ?-Cyclodextrin-Based Host-Guest Interactions towards Cancer Theranostics PubMed: Total synthesis of (ñ)-7-epi-nemorosone PubMed: Cryptic and Stereospecific Hydroxylation, Oxidation, and Reduction in Platensimycin and Platencin Biosynthesis PubMed: Effect of stevia aqueous extract on the antidiabetic activity of saxagliptin in diabetic rats PubMed: NF-?B/AP-1-targeted inhibition of macrophage-mediated inflammatory responses by depigmenting compound AP736 derived from natural 1,3-diphenylpropane skeleton PubMed: Pip-HoGu: An Artificial Assembly with Cooperative DNA Recognition Capable of Mimicking Transcription Factor Pairs PubMed: The synthetic retinoid ST1926 attenuates prostate cancer growth and potentially targets prostate cancer stem-like cells PubMed: Total Synthesis of Daphniphyllum Alkaloids: From Bicycles to Diversified Caged Structures PubMed: Saxagliptin alters bile acid profiles and yields metabolic benefits in drug-na‹ve overweight or obese type 2 diabetes patient PubMed: Metabolism, CB1 cannabinoid receptor binding and in vivo activity of synthetic cannabinoid 5F-AKB48: Implications for toxicity PubMed: Evaluation of Platensimycin and Platensimycin-Inspired Thioether Analogues against Methicillin-Resistant Staphylococcus aureus in Topical and Systemic Infection Mouse Models PubMed: Platensimycin and platencin: promising antibiotics for future application in human medicine PubMed: Platensimycin: a promising antimicrobial targeting fatty acid synthesis PubMed: SYSU-6, A New 2-D Aluminophosphate Zeolite Layer Precursor PubMed: Cytochrome P450-Catalyzed Hydroxylation Initiating Ether Formation in Platensimycin Biosynthesis PubMed: A Mutasynthetic Library of Platensimycin and Platencin Analogues PubMed: The boundary lipid around DMPC-spanning influenza A M2 transmembrane domain channels: Its structure and potential for drug accommodation PubMed: Place in therapy for liraglutide and saxagliptin for type 2 diabetes PubMed: Isothermal Titration Calorimetry Enables Rapid Characterization of Enzyme Kinetics and Inhibition for the Human Soluble Epoxide Hydrolase PubMed: Review of Platensimycin and Platencin: Inhibitors of ?-Ketoacyl-acyl Carrier Protein (ACP) Synthase III (FabH) PubMed: Solvophobically Driven Complexation of Adamantyl Mannoside with ?-Cyclodextrin in Water and Structured Organic Solvents PubMed: Saxagliptin attenuates glomerular podocyte injury by increasing the expression of renal nephrin and podocin in type 2 diabetic rats PubMed: Pharmaceuticals that contain polycyclic hydrocarbon scaffolds PubMed: Biosynthetic Origin of the Ether Ring in Platensimycin PubMed: Ezrin Inhibition Up-regulates Stress Response Gene Expression PubMed: Versatile Layer-By-Layer Highly Stable Multilayer Films: Study of the Loading and Release of FITC-Labeled Short Peptide in the Drug Delivery Field PubMed: Aminoadamantanes containing monoterpene-derived fragments as potent tyrosyl-DNA phosphodiesterase 1 inhibitors PubMed: The medium is the message: glycosphingolipids and their soluble analogues PubMed: Accurate Prediction of Bond Dissociation Energies and Barrier Heights for High-Energy Caged Nitro and Nitroamino Compounds Using a Coupled Cluster Theory PubMed: pH-Sensitive Micelles Based on Star Copolymer Ad-(PCL-b-PDEAEMA-b-PPEGMA)? for Controlled Drug Delivery PubMed: Improvement of secondary metabolite production in Streptomyces by manipulating pathway regulation PubMed: Single-Chain Glycopolymer Folding via Host-Guest Interactions and Its Unprecedented Effect on DC-SIGN Binding PubMed: Antibacterial, Mutagenic Properties and Chemical Characterisation of Sugar Bush (Protea caffra Meisn.): A South African Native Shrub Species PubMed: Semisynthesis of Platensimycin Derivatives with Antibiotic Activities in Mice via Suzuki-Miyaura Cross-Coupling Reactions PubMed: Crystal structures of cytochrome P-450CAM complexed with camphane, thiocamphor, and adamantane: factors controlling P-450 substrate hydroxylation PubMed: Perturbation Independent Decay of the Loschmidt Echo in a Many-Body System PubMed: Synthesis and antimicrobial evaluation of novel platensimycin analogues PubMed: Chemoprophylaxis of respiratory infections PubMed: Bioactive peptide functionalized aligned cyclodextrin nanofibers for neurite outgrowth PubMed: Efficacy and pharmacokinetics of OZ78 and MT04 against a natural infection with Fasciola hepatica in sheep PubMed: Recent advances in the chemotherapy of herpes virus infections PubMed: Cucurbit[7]uril-Driven Host-Guest Chemistry for Reversible Intervention of 5-Formylcytosine-Targeted Biochemical Reactions PubMed: Study of rimantadine in the USSR: a review of the literature PubMed: Corrigendum to 'anti-adipogenic adamantane type polycyclic polyprenylated acylphloroglucinols from Hypericum subsessile' Fitoterapia 147, (2020) 104755 PubMed: Stereocontrolled formal synthesis of (+/-)-platensimycin PubMed: Antibacterial sulfur-containing platensimycin and platencin congeners from Streptomyces platensis SB12029 PubMed: Biomimetic Stereoselective Sulfa-Michael Addition Leads to Platensimycin and Platencin Sulfur Analogues against Methicillin-Resistant Staphylococcus aureus PubMed: Platensimycin and platencin congeners from Streptomyces platensis PubMed: Synthesis, Biological Activities, and X-ray Crystal Structural Analysis of 25-Hydroxy-25(or 26)-adamantyl-17-[20(22),23-diynyl]-21-norvitamin D Compounds PubMed: Synthesis and biological evaluation of all eight stereoisomers of DPP-IV inhibitor saxagliptin PubMed: The bidirectional total synthesis of sampsonione P and hyperibone I PubMed: 7-Phenylplatensimycin and 11-methyl-7-phenylplatensimycin: more potent analogs of platensimycin PubMed: Discovery of a Structurally Unique Small Molecule that Inhibits Protein Synthesis PubMed: Quantitative determination of metformin, saxagliptin and 5-hydroxy saxagliptin simultaneously by hydrophilic interaction liquid chromatography - electrospray ionization mass spectrometry and its a PubMed: In vivo instability of platensimycin and platencin: Synthesis and biological evaluation of urea- and carbamate-platensimycin PubMed: [Development of novel drugs against influenza virus based on synthetic and natural compounds] PubMed: Construction of a smart temperature-responsive GPx mimic based on the self-assembly of supra-amphiphiles PubMed: Transformative hyaluronic acid-based active targeting supramolecular nanoplatform improves long circulation and enhances cellular uptake in cancer therapy PubMed: Mimicking natural globular structures with rigid scaffolds based on adamantane PubMed: Polycarbonate/Sulfonamide Composites with Ultralow Contents of Halogen-Free Flame Retardant and Desirable Compatibility PubMed: Layer by Layer Mesoporous Silica-Hyaluronic Acid-Cyclodextrin Bifunctional "Lamination": Study of the Application of Fluorescent Probe and Host?Guest Interactions in the Drug Delivery Field PubMed: A chemical genetic screen reveals that iminosugar inhibitors of plant glucosylceramide synthase inhibit root growth in Arabidopsis and cereals PubMed: Platensimycin activity against mycobacterial beta-ketoacyl-ACP synthases PubMed: Total synthesis and antibacterial properties of carbaplatensimycin PubMed: Mechanisms of self-resistance in the platensimycin- and platencin-producing Streptomyces platensis MA7327 and MA7339 strains PubMed: Synthesis of platensimycin analogues and their antibiotic potency PubMed: Antitumor activity of the synthetic retinoid ST1926 on primary effusion lymphoma in vitro and in vivo models PubMed: Origin of the unusual ultraviolet absorption of Arsenicin A PubMed: Titer improvement and pilot-scale production of platensimycin from Streptomyces platensis SB12026 PubMed: Comparison of glycemic control and ?-cell function in new onset T2DM patients with PCOS of metformin and saxagliptin monotherapy or combination treatment PubMed: Sustained Small Molecule Delivery from Injectable Hyaluronic Acid Hydrogels through Host-Guest Mediated Retention PubMed: DPP-4 inhibitor treatment: ?-cell response but not HbA(1c) reduction is dependent on the duration of diabetes PubMed: A supramolecular DNA self-assembly based on ?-cyclodextrin-adamantane complexation as a bioorthogonal sticky end motif PubMed: Dipeptidyl peptidase 8/9-like activity in human leukocytes PubMed: Dedicated ent-kaurene and ent-atiserene synthases for platensimycin and platencin biosynthesis PubMed: Oxyfunctionalization of non-natural targets by dioxiranes. 6. On the selective hydroxylation of cubane PubMed: Establishment of a dipeptidyl peptidases (DPP) 8/9 expressing cell model for evaluating the selectivity of DPP4 inhibitors PubMed: Isolation, structure and biological activities of platensimycin B4 from Streptomyces platensis PubMed: Discovery and exploitation of AZADO: the highly active catalyst for alcohol oxidation PubMed: Isolation, enzyme-bound structure and antibacterial activity of platencin A1 from Streptomyces platensis PubMed: Engineered Streptomyces platensis strains that overproduce antibiotics platensimycin and platencin PubMed: Redox-responsive mesoporous silica nanoparticles: a physiologically sensitive codelivery vehicle for siRNA and doxorubicin PubMed: Simultaneous staining of sputum smears for acid-fast and lipid-containing Myobacterium tuberculosis can enhance the clinical evaluation of antituberculosis treatments PubMed: Platensimycin and platencin biosynthesis in Streptomyces platensis, showcasing discovery and characterization of novel bacterial diterpene synthases PubMed: Proteomic signature of fatty acid biosynthesis inhibition available for in vivo mechanism-of-action studies PubMed: Construction of Hyaluronic Acid-Covered Hierarchically Porous MIL-nanoMOF for Loading and Controlled Release of Doxorubicin PubMed: Calcium-Permeable AMPA Receptors Mediate the Induction of the Protein Kinase A-Dependent Component of Long-Term Potentiation in the Hippocampus PubMed: Enhanced angiogenic effects of RGD, GHK peptides and copper (II) compositions in synthetic cryogel ECM model PubMed: Structure and semisynthesis of platensimide A, produced by Streptomyces platensis PubMed: ST1926, an orally active synthetic retinoid, induces apoptosis in chronic myeloid leukemia cells and prolongs survival in a murine model PubMed: Synthesis and biological evaluation of chromium bioorganometallics based on the antibiotic platensimycin lead structure PubMed: The binding interaction of synthetic ozonide antimalarials with natural and modified beta-cyclodextrins PubMed: A genetically amenable platensimycin- and platencin-overproducer as a platform for biosynthetic explorations: a showcase of PtmO4, a long-chain acyl-CoA dehydrogenase PubMed: Expression and characterization of an epoxide hydrolase from Anopheles gambiae with high activity on epoxy fatty acids PubMed: Blockade of neurotensin receptors affects differently hypo-locomotion and catalepsy induced by haloperidol in mice PubMed: Isoplatensimycin: Synthesis and biological evaluation PubMed: Computational NMR spectroscopy of organoarsenicals and the natural polyarsenic compound arsenicin A PubMed: [HIV-inhibiting activity of polyanion matrices and related substances containing adamantane and norbornene pharmacophores] PubMed: Antimalarial activity of artefenomel (OZ439), a novel synthetic antimalarial endoperoxide, in patients with Plasmodium falciparum and Plasmodium vivax malaria: an open-label phase 2 trial PubMed: A Simple Strategy to Construct Amorphous Metal-Free Room Temperature Phosphorescent and Multi-Color Materials PubMed: Construction of a smart microgel glutathione peroxidase mimic based on supramolecular self-assembly PubMed: Bioactive acylphloroglucinols with adamantyl skeleton from Hypericum sampsonii PubMed: H1N1 2009 pandemic influenza virus: resistance of the I223R neuraminidase mutant explained by kinetic and structural analysis PubMed: Trace analysis of total naphthenic acids in aqueous environmental matrices by liquid chromatography/mass spectrometry-quadrupole time of flight mass spectrometry direct injection PubMed: Adamantyl globotriaosyl ceramide: a monovalent soluble mimic which inhibits verotoxin binding to its glycolipid receptor PubMed: Structures of Pseudomonas aeruginosa ?-ketoacyl-(acyl-carrier-protein) synthase II (FabF) and a C164Q mutant provide templates for antibacterial drug discovery and identify a buried potassium ion PubMed: Saxagliptin added to a thiazolidinedione improves glycemic control in patients with type 2 diabetes and inadequate control on thiazolidinedione alone PubMed: A chemiluminescent substrate for the detection of phosphatidylinositol-specific phospholipase C PubMed: Synthesis of an Efficient S/N-Based Flame Retardant and Its Application in Polycarbonate PubMed: Metabolic mimics: thiol responsive drug release PubMed: (-)-Adamantyl-delta8-tetrahydrocannabinol (AM-411), a selective cannabinoid CB1 receptor agonist: effects on open-field behaviors and antagonism by SR-141716 in rats PubMed: Stereodivergent resolution of oxabicyclic ketones: preparation of key intermediates for platensimycin and other natural products PubMed: Emergence of H5N1 avian influenza viruses with reduced sensitivity to neuraminidase inhibitors and novel reassortants in Lao People's Democratic Republic PubMed: Acetylcholine-like and trimethylglycine-like PTA (1,3,5-triaza-7-phosphaadamantane) derivatives for the development of innovative Ru- and Pt-based therapeutic agents PubMed: Synthesis and optimization of a new family of type 3 17 beta-hydroxysteroid dehydrogenase inhibitors by parallel liquid-phase chemistry PubMed: Mechanism for photosynthetic O2 evolution PubMed: Coronavirus helicases: attractive and unique targets of antiviral drug-development and therapeutic patents PubMed: FT-IR and FT-Raman spectroscopic signatures, vibrational assignments, NBO, NLO analysis and molecular docking study of 2-{[5-(adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N,N-dimethyle PubMed: Total synthesis of (-)-platensimycin, a novel antibacterial agent PubMed: Isolation, structure and biological activities of platencin A(2)-A(4) from Streptomyces platensis PubMed: A carbonyl ylide cycloaddition approach to platensimycin PubMed: Syntheses and crystal structures of a series of coordination polymers constructed from C2-symmetric ligand 1,3-adamantanedicarboxylic acid PubMed: Local correlation domains for coupled cluster theory: optical rotation and magnetic-field perturbations PubMed: Diamondoid diacids ('O4' species) in oil sands process-affected water PubMed: Illumination with ultraviolet or visible light induces chemical changes in the water-soluble manganese complex, [Mn(4)O(6)(bpea)(4)]Br(4) PubMed: Total synthesis of plukenetione A PubMed: Identification of a highly potent vitamin D receptor antagonist: (25S)-26-adamantyl-25-hydroxy-2-methylene-22,23-didehydro-19,27-dinor-20-epi-vitamin D3 (ADMI3) PubMed: Topographic recognition of cyclic hydrocarbons and related compounds by receptors for androgens, estrogens, and glucocorticoids PubMed: Isolation, structure and fatty acid synthesis inhibitory activities of platensimycin B1-B3 from Streptomyces platensis PubMed: Oxyfunctionalization of non-natural targets by dioxiranes. 5. Selective oxidation of hydrocarbons bearing cyclopropyl moieties PubMed: CQMUH-011 mitigates autoimmune hepatitis via inhibiting the function of T lymphocytes PubMed: A full topological analysis of unstable and metastable bond critical points PubMed: [Combined action of antiviral substances of natural and synthetic origin. I. The anti-influenza action of a combination of the polyphenol complex isolated from Geranium sanguineum L. and remantadi PubMed: Structural and spectroscopic characterization of a novel potential anti-inflammatory agent 3-(adamantan-1-yl)-4-ethyl-1H-1,2,4-triazole-5(4H)thione by first principle calculations PubMed: Single-electron self-exchange between cage hydrocarbons and their radical cations in the gas phase PubMed: Chemically responsive supramolecular assemblies of pyrene-beta-cyclodextrin dimer PubMed: Vaccination as a strategy to reduce the emergence of amantadine- and rimantadine-resistant strains of A/Chick/Pennsylvania/83 (H5N2) influenza virus PubMed: Modification of "peptoid" CCK-B antagonists to probe requirements for CCK-B agonist activity PubMed: Chemotherapy and vaccination: a possible strategy for the control of highly virulent influenza virus PubMed: [Interferonogenic and antiviral activity of the double-stranded replicative form of phage f2 RNA in tissue culture and on animals] PubMed: Role of K+ATP channels and EDRF in reactive hyperemia in the hindquarters vascular bed of cats PubMed: Observation of a stable carbocation in a consecutive criegee rearrangement with trifluoroperacetic acid