| Name: | methyl(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate |
| CAS Number: | 146-48-5 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 205-672-0 |
| FDA UNII: | 2Y49VWD90Q |
| Nikkaji Web: | J9.366A |
| Beilstein Number: | 0097276 |
| XlogP3: | 2.90 (est) |
| Molecular Weight: | 354.44982000 |
| Formula: | C21 H26 N2 O3 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:pharmaceuticals / chemical synthisis
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Melting Point: | 241.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 542.98 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 540.00 °F. TCC ( 282.20 °C. ) (est)
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| logP (o/w): | 2.730 |
| Soluble in: |
| | water, 401.8 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
oral-human TDLo 643 ug/kg/3W-I
BEHAVIORAL: EXCITEMENT
VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Life Sciences. Vol. 30, Pg. 2033, 1982.
oral-man TDLo 694 ug/kg/3D-I
SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
British Journal of Psychiatry. Vol. 169, Pg. 384, 1996.
intraperitoneal-mouse LD50 16 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
oral-mouse LD50 43 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
intravenous-rabbit LDLo 11 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1418, 1935.
|
| Dermal Toxicity: |
subcutaneous-mouse LD50 37 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
subcutaneous-rabbit LDLo 50 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1418, 1935.
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | pharmaceuticals / chemical synthisis |
| Recommendation for yohimbine usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for yohimbine flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| EPI System: View |
| ClinicalTrials.gov:search |
| Daily Med:search |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :8969 |
| National Institute of Allergy and Infectious Diseases:Data |
| methyl(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate |
| Chemidplus:0000146485 |
| RTECS:ZG1000000 for cas# 146-48-5 |
References:
| | methyl(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 8969 |
| Pubchem (sid): | 134974784 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | aphrodine | | 17- | hydroxy-yohimbane-16-carboxylic acid methyl ester | | (16a,17a)-17- | hydroxyyohimban-16-carboxylic acid methyl ester | | 17- | hydroxyyohimban-16-carboxylic acid methyl ester | | | johimbin | | | methyl (16a,17a)-17-hydroxyyohimban-16-carboxylate | | | methyl 17a-hydroxyyohimban-16a-carboxylate | | | methyl(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate | | | quebrachin | | | quebrachine | | | yohimban-16-a-carboxylic acid, 17-a-hydroxy-, methyl ester | | | yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16a,17a)- | | | yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16a,17a)- (9CI) | | | yohimban-16a-carboxylic acid, 17a-hydroxy-, methyl ester (8CI) | | | yohimbic acid methyl ester | | | yohimbin | | (+)- | yohimbin | | (+)- | yohimbine | | | yohimbol-16a-carboxylic acid, methyl ester (6CI) |
Articles:
| PubMed:Effect of yohimbine on reinstatement of operant responding in rats is dependent on cue contingency but not food reward history. |
| PubMed:Pharmacological Evidence of α2-Adrenergic Receptors in the Hypotensive Effect of Platonia insignis Mart. |
| PubMed:Sexual Enhancement Products for Sale Online: Raising Awareness of the Psychoactive Effects of Yohimbine, Maca, Horny Goat Weed, and Ginkgo biloba. |
| PubMed:Inactivation of the nucleus accumbens core or medial shell attenuates reinstatement of sugar-seeking behavior following sugar priming or exposure to food-associated cues. |
| PubMed:A cocktail of synthetic stimulants found in a dietary supplement associated with serious adverse events. |
| PubMed:Synthesis of 2´-hydroxy-4´-Isoprenyloxychalcone Derivatives with Potential Antidepressant-Like Activity. |
| PubMed:Effects of Dates Pulp Extract and Palm Sap (Phoenix dactylifera L.) on Gastrointestinal Transit Activity in Healthy Rats. |
| PubMed:Acute stressor effects on goal-directed action in rats. |
| PubMed:Genetic inactivation of pleiotrophin but not midkine potentiates clonidine-induced alpha-2 adrenergic-mediated analgesia. |
| PubMed:Synthesis of 2,4-dihydroxychalcone derivatives as potential antidepressant effect. |
| PubMed:The selective dopamine β-hydroxylase inhibitor nepicastat attenuates multiple aspects of cocaine-seeking behavior. |
| PubMed:Optogenetic inhibition of dorsal medial prefrontal cortex attenuates stress-induced reinstatement of palatable food seeking in female rats. |
| PubMed:Ethopharmacological evaluation of the rat exposure test: a prey-predator interaction test. |
| PubMed:Antagonism of the neuropeptide S receptor with RTI-118 decreases cocaine self-administration and cocaine-seeking behavior in rats. |
| PubMed:Simultaneous glucocorticoid and noradrenergic activity disrupts the neural basis of goal-directed action in the human brain. |
| PubMed:Pregabalin reduces cocaine self-administration and relapse to cocaine seeking in the rat. |
| PubMed:Medial prefrontal cortex neuronal activation and synaptic alterations after stress-induced reinstatement of palatable food seeking: a study using c-fos-GFP transgenic female rats. |
| PubMed:A comparison of dehydroepiandrosterone and 7-keto dehydroepiandrosterone with other drugs that modulate ethanol intake in rats responding under a multiple schedule. |
| PubMed:Chromatographic fingerprint analysis of yohimbe bark and related dietary supplements using UHPLC/UV/MS. |
| PubMed:Detection of hazardous weight-loss substances in adulterated slimming formulations using ultra-high-pressure liquid chromatography with diode-array detection. |
| PubMed:Effect of fenfluramine on reinstatement of food seeking in female and male rats: implications for the predictive validity of the reinstatement model. |
| PubMed:Profiling the indole alkaloids in yohimbe bark with ultra-performance liquid chromatography coupled with ion mobility quadrupole time-of-flight mass spectrometry. |
| PubMed:Pregabalin reduces alcohol drinking and relapse to alcohol seeking in the rat. |
| PubMed:Alpha1 receptor antagonist in the median raphe nucleus evoked hyperphagia in free-feeding rats. |
| PubMed:Erectile dysfunction. |
| PubMed:Agmatine in the hypothalamic paraventricular nucleus stimulates feeding in rats: involvement of neuropeptide Y. |
| PubMed:A novel approach to simultaneous screening and confirmation of regulated pharmaceutical compounds in dietary supplements by LC/MS/MS with an information-dependent acquisition method. |
| PubMed:Effect of prazosin and guanfacine on stress-induced reinstatement of alcohol and food seeking in rats. |
| PubMed:Activation of nuclear PPARγ receptors by the antidiabetic agent pioglitazone suppresses alcohol drinking and relapse to alcohol seeking. |
| PubMed:Deepened extinction following compound stimulus presentation: noradrenergic modulation. |
| PubMed:Pharmacokinetics of yohimbine following intravenous administration to horses. |
| PubMed:Octopamine and occupancy: an aminergic mechanism for intruder-resident aggression in crickets. |
| PubMed:Role of dorsal medial prefrontal cortex dopamine D1-family receptors in relapse to high-fat food seeking induced by the anxiogenic drug yohimbine. |
| PubMed:Concurrent glucocorticoid and noradrenergic activity shifts instrumental behavior from goal-directed to habitual control. |
| PubMed:Simultaneous determination of yohimbine, sildenafil, vardenafil and tadalafil in dietary supplements using high-performance liquid chromatography-tandem mass spectrometry. |
| PubMed:Adverse drug events associated with yohimbine-containing products: a retrospective review of the California Poison Control System reported cases. |
| PubMed:Long-Evans rats acquire operant self-administration of 20% ethanol without sucrose fading. |
| PubMed:Role of CRF and other neuropeptides in stress-induced reinstatement of drug seeking. |
| PubMed:Central administration of somatostatin stimulates feeding behavior in chicks. |
| PubMed:The neuropharmacology of relapse to food seeking: methodology, main findings, and comparison with relapse to drug seeking. |
| PubMed:A novel operant conflict procedure using incrementing shock intensities to assess the anxiolytic and anxiogenic effects of drugs. |
| PubMed:Effects of the MCH1 receptor antagonist SNAP 94847 on high-fat food-reinforced operant responding and reinstatement of food seeking in rats. |
| PubMed:Role of adrenergic alpha-2-receptors on feeding behavior in layer-type chicks. |
| PubMed:Central administration of galanin stimulates feeding behavior in chicks. |
| PubMed:Simultaneous determination of thirteen plant alkaloids in a human specimen by SPE and HPLC. |
| PubMed:Inhibition of orexin-1/hypocretin-1 receptors inhibits yohimbine-induced reinstatement of ethanol and sucrose seeking in Long-Evans rats. |
| PubMed:A comparison of the effects of different operant training experiences and dietary restriction on the reinstatement of cocaine-seeking in rats. |
| PubMed:Differential effects of the hypocretin 1 receptor antagonist SB 334867 on high-fat food self-administration and reinstatement of food seeking in rats. |
| PubMed:Peptide YY3-36 decreases reinstatement of high-fat food seeking during dieting in a rat relapse model. |
| PubMed:Role of alpha2 receptors in quercetin-induced behavioral despair in mice. |
| PubMed:Noradrenergic inputs to the bed nucleus of the stria terminalis and paraventricular nucleus of the hypothalamus underlie hypothalamic-pituitary-adrenal axis but not hypophagic or conditioned avoidance responses to systemic yohimbine. |
| PubMed:Role of food type in yohimbine- and pellet-priming-induced reinstatement of food seeking. |
| PubMed:The contractile effect of the ghrelin receptor antagonist, D-Lys3-GHRP-6, in rat fundic strips is mediated through 5-HT receptors. |
| PubMed:Participation of alpha2 receptors in the antinociceptive activity of quercetin. |
| PubMed:A comparison of the effects of psychotomimetics and anxiolytics on punished and unpunished responding maintained by fixed interval schedules of food reinforcement in the rat. |
| PubMed:The anxiogenic drug yohimbine reinstates palatable food seeking in a rat relapse model: a role of CRF1 receptors. |
| PubMed:The HND mouse, a nonobese model of type 2 diabetes mellitus with impaired insulin secretion. |
| PubMed:The anxiogenic drug yohimbine activates central viscerosensory circuits in rats. |
| PubMed:An oral yohimbine/L-arginine combination (NMI 861) for the treatment of male erectile dysfunction: a pharmacokinetic, pharmacodynamic and interaction study with intravenous nitroglycerine in healthy male subjects. |
| PubMed:Alpha2-adrenoceptor modulation of long-term potentiation elicited in vivo in rat occipital cortex. |
| PubMed:Endothelin-like action of Pausinystalia yohimbe aqueous extract on vascular and renal regional hemodynamics in Sprague Dawley rats. |
| PubMed:A review of plant-derived and herbal approaches to the treatment of sexual dysfunctions. |
| PubMed:Some sweet and bitter tastants stimulate inhibitory pathway of adenylyl cyclase via melatonin and alpha 2-adrenergic receptors in Xenopus laevis melanophores. |
| PubMed:The role of catecholamines in retention performance of a partially baited radial eight-arm maze for rats. |
| PubMed:Neuromedin U acts in the central nervous system to inhibit gastric acid secretion via CRH system. |
| PubMed:Neural activation profile elicited by cues associated with the anxiogenic drug yohimbine differs from that observed for reward-paired cues. |
| PubMed:Gastrointestinal transit in mice treated with various extracts of date (Phoenix dactylifera L.). |
| PubMed:Intracerebroventricular administration of octopamine stimulates food intake of chicks through alpha(2)-adrenoceptor. |
| PubMed:Alpha2 -adrenoceptor function in arterial hypertension associated with obesity in dogs fed a high-fat diet. |
| PubMed:Summary for patients. Liver failure associated with the dietary supplement LipoKinetix. |
| PubMed:Balancing safety of dietary supplements with the free market. |
| PubMed:Severe hepatotoxicity associated with the dietary supplement LipoKinetix. |
| PubMed:Food deprivation increases alpha(2)-adrenoceptor-mediated modulation of jejunal epithelial transport in young and adult rats. |
| PubMed:Yohimbine use in a natural setting: effects on posttraumatic stress disorder. |
| PubMed:Sildenafil in the treatment of female sexual dysfunction induced by selective serotonin reuptake inhibitors. |
| PubMed:Noradrenergic modulation of the discriminative-stimulus effects of methamphetamine in rats. |
| PubMed:Histamine regulates food intake through modulating noradrenaline release in the para-ventricular nucleus. |
| PubMed:Locus coeruleus-mediated inhibition of chemosensory responses in the rat nucleus tractus solitarius is mediated by alpha2-adrenoreceptors. |
| PubMed:Discriminative stimulus effects of 8-hydroxy-2-(di-n-propylamino)tetralin in pigeons and rats: species similarities and differences. |
| PubMed:Evaluation of the effects of a specific alpha 2-adrenoceptor antagonist, atipamezole, on alpha 1- and alpha 2-adrenoceptor subtype binding, brain neurochemistry and behaviour in comparison with yohimbine. |
| PubMed:Extralabel use of tranquilizers and general anesthetics. |
| PubMed:Anxiogenic action of caffeine: an experimental study in rats. |
| PubMed:Enhancement of central noradrenaline release during development alters the packing density of neurons in the rat occipital cortex. |
| PubMed:Local administration of dopaminergic drugs into the ventral tegmental area modulates cataplexy in the narcoleptic canine. |
| PubMed:Antinociceptive effects of neuropeptide Y and related peptides in mice. |
| PubMed:Discriminative-stimulus effects of morphine in combination with alpha- and beta-noradrenergic agonists and antagonists in rats. |
| PubMed:[Clinical investigations of an i.m. combination anesthesia with fentanylclimazolam/xylazine and postoperative i.v. antagonism with naloxone/sarmazenil/yohimbine in guinea pigs]. |
| PubMed:Drugs coordinating and restoring gastrointestinal motility and their effect on selected hypodynamic gastrointestinal disorders in horses and cattle. |
| PubMed:Gas chromatographic determination of yohimbine in commercial yohimbe products. |
| PubMed:Determination of ajmalicine in reserpine raw materials by liquid chromatography with fluorescence detection. |
| PubMed:The galanin-induced feeding stimulation is mediated via alpha 2-adrenergic receptors in goldfish. |
| PubMed:Anxiogenic activity of intraventricularly administered bradykinin in rats. |
| PubMed:Vasopressin inhibits food intake in pygmy goats by activation of alpha 1-adrenergic receptors. |
| PubMed:Potential risks of health food products containing yohimbe extracts. |
| PubMed:Regulation of gastrin release in the dog by alpha 2-adrenoceptors. |
| PubMed:The role of adrenoreceptors in control of stereotyped oral behavior in restricted-fed fowls. |
| PubMed:Cholinergic regulation of cataplexy in canine narcolepsy in the pontine reticular formation is mediated by M2 muscarinic receptors. |
| PubMed:Evidence that 5-HT2c receptor antagonists are anxiolytic in the rat Geller-Seifter model of anxiety. |
| PubMed:The discriminative stimulus effects of cocaine in pigeons. |
| PubMed:An assessment of the involvement of paraventricular hypothalamic alpha 2-adrenoceptors in phenylpropanolamine anorexia. |
| PubMed:Potentiation of dark onset feeding in obese mice (genotype ob/ob) following central injection of norepinephrine and clonidine. |
| PubMed:Commercially marketed supplements for bodybuilding athletes. |
| PubMed:Specificity of alpha- and beta-adrenergic inhibition of water and food intake. |
| PubMed:[The participation of neuropeptide Y and the catecholaminergic systems of the brain in feeding behavior]. |
| PubMed:Yohimbine attenuates clonidine-induced feeding and macronutrient selection in genetically obese (ob/ob) mice. |
| PubMed:Evidence for noradrenergic involvement in mediating the FG 7142 discriminative stimulus. |
| PubMed:Isolated failure of noradrenergic transmission in a case with orthostatic hypotension and hyperactivity of gastro-colic reflex. |
| PubMed:Insulin secretion from ob/ob mouse pancreatic islets: effects of neurotransmitters. |
| PubMed:Potentiation of carbon tetrachloride hepatotoxicity by phenylpropanolamine. |
| PubMed:Anorectic effect of alpha 2-antagonists in dog: effect of acute and chronic treatment. |
| PubMed:Stimulation of food intake in rats by the alpha 2-adrenoceptor agonists xylazine and detomidine. |
| PubMed:Inverse agonist properties of the THBC discriminative stimulus: asymmetrical generalization with FG 7142. |
| PubMed:Yohimbine early in life alters functional properties of interhemispheric connections of rat visual cortex. |
| PubMed:Neuropeptide Y and catecholamine-mediated neuronal transmission in mechanisms of feeding-behaviour induction. |
| PubMed:Discriminative stimulus effect of phenylephrine. |
| PubMed:Bimodal effect of neuropeptide Y on feeding, and its antagonism by receptor blocking agents in rats. |
| PubMed:Associative influences on tolerance to decreased fixed-interval responding by clonidine. |
| PubMed:[Evaluation of the effect of yohimbine, an alpha2 adrenolytic drug, on gastric emptying in obesity]. |
| PubMed:Amnesic trace locked into the benzodiazepine state of memory. |
| PubMed:Metabolism of inositol phosphates in alpha 1-adrenoceptor-stimulated and homogenized cardiac myocytes of adult rats. |
| PubMed:M-octopamine injected into the paraventricular nucleus induces eating in rats: a comparison with noradrenaline-induced eating. |
| PubMed:A pharmacological analysis of food intake regulation in rats treated neonatally with monosodium L-glutamate (MSG). |
| PubMed:Further characterization of the discriminative stimulus effects of buspirone using monoamine agonists and antagonists in the pigeon. |
| PubMed:Effect of metalaxyl on heart rate in rats: role of alpha 1-adrenoreceptors. |
| PubMed:Sensitivity of pentylenetetrazol discrimination increased by a stimulus fading technique. |
| PubMed:Evidence for antiserotonergic properties of yohimbine. |
| PubMed:Cholecystokinin modulation of [3H]noradrenaline release from superfused hypothalamic slices. |
| PubMed:Evaluation of antagonists of the discriminative stimulus and response rate effects of phencyclidine. |
| PubMed:Behavioural effects of the alpha 2-adrenoceptor antagonists idazoxan and yohimbine in rats: comparisons with amphetamine. |
| PubMed:Alpha 2-adrenoceptor blockade attenuates feeding behavior induced by neuropeptide Y and epinephrine. |
| PubMed:The alpha 2-adrenoceptor antagonists idazoxan and yohimbine increase rates of DRL responding in rats. |
| PubMed:Enhancement of a diazepam withdrawal symptom by bicuculline and yohimbine. |
| PubMed:Learning enhancement and behavioral arousal induced by yohimbine. |
| PubMed:Clonidine suppression and its adrenoreceptor mediation in schedule-induced polydipsia. |
| PubMed:Delayed up-regulation of alpha-adrenoceptor populations in particular regions of the rat brain after stimulation of the nucleus locus coeruleus. |
| PubMed:Serotonergic mediation of tetrahydro-beta-carboline. |
| PubMed:Single unit activity of locus coeruleus neurons in the freely moving cat. II. Conditioning and pharmacologic studies. |
| PubMed:Apomorphine anorexia: a further pharmacological characterization. |
| PubMed:Discriminative stimulus properties of xylazine in rat: discriminability and effects of putative alpha-2 adrenoceptor agonists and antagonists. |
| PubMed:One-way generalization of clonidine to the discriminative stimulus produced by cocaine. |
| PubMed:Tolerance to or facilitation of pharmacological effects induced by chronic treatment with the beta-adrenergic stimulant clenbuterol. |
| PubMed:Discriminative stimuli produced by clonidine in spontaneously hypertensive rats: generalization to antihypertensive drugs with different mechanisms of action. |
| PubMed:The effect of antidepressant drugs on dominance behavior in rats competing for food. |
| PubMed:Effects of the training dose on generalization of morphine stimulus to clonidine. |
| PubMed:Evidence against the involvement of a noradrenergic mechanism in the release by diazepam of novelty-induced hypophagia in rats. |
| PubMed:Yohimbine and rauwolscine reduce food intake of genetically obese (obob) and lean mice. |
| PubMed:Brain amine metabolism is reflected in cerebral ventricular CSF. |
| PubMed:Adrenergic activation of triiodothyronine production in brown adipose tissue. |
| PubMed:Effects of clonidine on operant behavior and electric shock titration in the squirrel monkey: effects of alpha 2-adrenoreceptor antagonism. |
| PubMed:Pharmacological manipulation of sincalide (CCK-8)-induced suppression of feeding. |
| PubMed:An analysis of the effects of systemically administered clonidine on the food and water intake of rats. |
| PubMed:Discriminative stimuli produced by clonidine: an investigation of the possible relationship to adrenoceptor stimulation and hypotension. |
| PubMed:Clonidine analgesia and suppression of operant responding: dissociation of mechanism. |
| PubMed:Clonidine-induced hyperphagia in monkeys: evidence for alpha 2-noradrenergic receptor mediation. |
| PubMed:Clonidine increases food and protein consumption in rats. |
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